TSQ / Townsquare Media, Inc. - تصريحات هيئة الأوراق المالية والبورصات، التقرير السنوي، بيان الوكيل

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): August 6, 2025 Townsquare Media,

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): August 6, 2025 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizatio

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 ☐ TRANSITION REPORT PURSUANT TO S

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc.

TOWNSQUARE BEATS Q2 ADJUSTED EBITDA GUIDE AS ADJUSTED EBITDA EXCLUDING POLITICAL INCREASES +4% YOY Digital Represents 55% of 1H’25 Net Revenue and 56% of 1H’25 Segment Profit Repurchased $10 Million of Debt in Q2’25 and $13 Million of Debt Since the

IMMEDIATE RELEASE TOWNSQUARE BEATS Q2 ADJUSTED EBITDA GUIDE AS ADJUSTED EBITDA EXCLUDING POLITICAL INCREASES +4% YOY Digital Represents 55% of 1H’25 Net Revenue and 56% of 1H’25 Segment Profit Repurchased $10 Million of Debt in Q2’25 and $13 Million of Debt Since the February 2025 Refinancing Purchase, NY – August 6, 2025 - Townsquare Media, Inc.

TOWNSQUARE BEATS Q1 ADJUSTED EBITDA GUIDE AND REAFFIRMS FULL YEAR GUIDANCE AS A RESULT OF STRONG DIGITAL REVENUE AND PROFIT GROWTH Q1 Total Digital Revenue +6.4% YOY and Total Digital Segment Profit +16.2% YOY Digital Represents 57% of Q1 Net Revenue

IMMEDIATE RELEASE TOWNSQUARE BEATS Q1 ADJUSTED EBITDA GUIDE AND REAFFIRMS FULL YEAR GUIDANCE AS A RESULT OF STRONG DIGITAL REVENUE AND PROFIT GROWTH Q1 Total Digital Revenue +6.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 ☐ TRANSITION REPORT PURSUANT TO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): May 8, 2025 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organization)

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): May 6, 2025 (May 1, 2025) Townsquare Media, Inc. (Exact name of Registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or

SCHEDULE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Definitive Proxy State

SCHEDULE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) x Defin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc. (Ex

TOWNSQUARE DELIVERS NET REVENUE AND ADJUSTED EBITDA GROWTH IN Q4 2024 ANNOUNCES INCREASE IN DIVIDEND Total Digital Net Revenue Growth of +10.8% in Q4 2024 Townsquare Ignite (Digital Advertising) Net Revenue Growth of +15.5% in Q4 2024 Repurchased $36

IMMEDIATE RELEASE TOWNSQUARE DELIVERS NET REVENUE AND ADJUSTED EBITDA GROWTH IN Q4 2024 ANNOUNCES INCREASE IN DIVIDEND Total Digital Net Revenue Growth of +10.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): March 17, 2025 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizatio

List of Subsidiaries of Townsquare Media, Inc.

Exhibit 21.1 Subsidiaries of Townsquare Media, Inc. Exact Name of Subsidiaries of Registrant Jurisdiction of Incorporation or Organization Townsquare Live Events International, LLC Delaware Townsquare Next, LLC Delaware Townsquare Live Productions, LLC Delaware Townsquare Interactive, LLC Delaware Townsquare MMN, LLC Delaware Townsquare Commerce, LLC Delaware Townsquare Finance, LLC Delaware Towns

Insider Trading Policy

Exhibit 19.1 INSIDER TRADING POLICY TOWNSQUARE MEDIA, INC. PURPOSE This Insider Trading Policy (the “Policy”) provides guidelines with respect to transactions in the securities of Townsquare Media, Inc. (the “Company”) and the handling of confidential information about the Company and the companies with which the Company does business. The Company’s Board of Directors (the “Board”) has adopted thi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): February 19, 2025 Townsquare Medi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): February 19, 2025 Townsquare Media, Inc. (Exact name of Registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organiza

Security Agreement dated as of February 19, 2025, among the Company, the guarantors party thereto and Bank of America, N.A., as collateral agent.

Execution Version SECURITY AGREEMENT Dated February 19, 2025 among The Grantors referred to herein, as Grantors and BANK OF AMERICA, N.

Credit Agreement dated as of February 19, 2025, among the Company, Bank of America, N.A., as administrative agent and collateral agent, and the lenders and financial institutions party thereto

Execution Version CREDIT AGREEMENT DATED AS OF FEBRUARY 19, 2025 AMONG TOWNSQUARE MEDIA, INC.

TOWNSQUARE MEDIA, INC. REPORTS PRELIMINARY ESTIMATED 2024 RESULTS

IMMEDIATE RELEASE TOWNSQUARE MEDIA, INC. REPORTS PRELIMINARY ESTIMATED 2024 RESULTS Purchase, NY - January 21, 2025 - Townsquare Media, Inc. (NYSE: TSQ) (“Townsquare”, the "Company," "we," "us," or "our") announced today preliminary estimated financial results for the fourth quarter and full year ended December 31, 2024. “We are pleased to pre-announce our fourth quarter and full year 2024 estimat

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): January 21, 2025 Townsquare Media, Inc. (Exact name of Registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizat

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): December 10, 2024 Townsquare Media, Inc. (Exact name of Registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organiza

Joint Filing Agreement dated November 14, 2024

EX-99.1 2 d841017dex991.htm EX-99.1 CUSIP No. 892231101 Exhibit 99.1 AGREEMENT REGARDING THE JOINT FILING OF SCHEDULE 13G The undersigned hereby agree as follows: (i) Each of them is individually eligible to use the Schedule 13G to which this Exhibit is attached, and such Schedule 13G is filed on behalf of each of them; and (ii) Each of them is responsible for the timely filing of such Schedule 13

TSQ / Townsquare Media, Inc. / MSD CAPITAL L P - SC 13G/A Passive Investment

SC 13G/A CUSIP No. 892231101 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 3)* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 892231101 (CUSIP Number) September 30, 2024 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to desi

TSQ / Townsquare Media, Inc. / AMERICAN CENTURY INVESTMENT MANAGEMENT INC - SC 13G/A Passive Investment

SC 13G/A 1 townsquaremedia13g-a5.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 5) * TOWNSQUARE MEDIA, INC. (Name of Issuer) CLASS A COMMON STOCK (Title of Class of Securities) 892231101 (CUSIP Number) SEPTEMBER 30, 2024 (Date of Event Which Requires Filing of this Statement) Check the appro

TOWNSQUARE RETURNS TO TOTAL AND DIGITAL REVENUE GROWTH IN THE THIRD QUARTER Digital Represents 52% of September YTD Total Net Revenue Ignite's Digital Advertising Revenue Growth Accelerates in Q3 Repurchased $25 Million of Debt ($36M through October)

IMMEDIATE RELEASE TOWNSQUARE RETURNS TO TOTAL AND DIGITAL REVENUE GROWTH IN THE THIRD QUARTER Digital Represents 52% of September YTD Total Net Revenue Ignite's Digital Advertising Revenue Growth Accelerates in Q3 Repurchased $25 Million of Debt ($36M through October) and $24 Million of Equity in September YTD Period Purchase, NY – November 7, 2024 - Townsquare Media, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 ☐ TRANSITION REPORT PURSUANT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media,

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): November 7, 2024 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizat

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): August 7, 2024 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizatio

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 ☐ TRANSITION REPORT PURSUANT TO S

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc.

TOWNSQUARE DRIVES SEQUENTIAL IMPROVEMENT IN SECOND QUARTER Digital Represents 52% of 1H'24 Total Net Revenue Repurchased $14 Million of Debt and $22 Million of Equity in 1H’24

IMMEDIATE RELEASE TOWNSQUARE DRIVES SEQUENTIAL IMPROVEMENT IN SECOND QUARTER Digital Represents 52% of 1H'24 Total Net Revenue Repurchased $14 Million of Debt and $22 Million of Equity in 1H’24 Purchase, NY – August 7, 2024 - Townsquare Media, Inc.

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July 23, 2024 Via EDGAR United States Securities and Exchange Commission Division of Corporation Finance Office of Technology 100 F Street, NE Washington, D.

As filed with the Securities and Exchange Commission on July 2, 2024

As filed with the Securities and Exchange Commission on July 2, 2024 Registration No.

Filing Fees Table (filed herewith)

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) Townsquare Media, Inc.

2014 Omnibus Incentive Plan

Exhibit 99.1 AMENDED AND RESTATED TOWNSQUARE MEDIA, INC. 2014 OMNIBUS INCENTIVE PLAN ARTICLE I PURPOSE The purpose of this Amended and Restated Townsquare Media, Inc. 2014 Omnibus Incentive Plan is to enhance the profitability and value of the Company for the benefit of its stockholders by enabling the Company to offer Eligible Individuals cash and stock-based incentives in order to attract, retai

As filed with the Securities and Exchange Commission on July 2, 2024

As filed with the Securities and Exchange Commission on July 2, 2024 No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 POST-EFFECTIVE AMENDMENT NO. 1 TO FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 27-1996555 (State or other jurisdiction of incorporation or orga

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): May 10, 2024 (May 9, 2024) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): May 9, 2024 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organization)

``````````````````````````` UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 ☐ TR

``````````````````````````` UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

TOWNSQUARE ANNOUNCES FIRST QUARTER RESULTS THAT DEMONSTRATE IMPROVEMENT ACROSS ALL BUSINESS SEGMENTS; TOWNSQUARE INTERACTIVE RETURNS TO SUBSCRIBER GROWTH AND MONTH-OVER-MONTH REVENUE GROWTH IN MARCH AND APRIL Digital Represents 53% of First Quarter T

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES FIRST QUARTER RESULTS THAT DEMONSTRATE IMPROVEMENT ACROSS ALL BUSINESS SEGMENTS; TOWNSQUARE INTERACTIVE RETURNS TO SUBSCRIBER GROWTH AND MONTH-OVER-MONTH REVENUE GROWTH IN MARCH AND APRIL Digital Represents 53% of First Quarter Total Net Revenue and Adjusted Operating Income Purchase, NY – May 9, 2024 - Townsquare Media, Inc.

TSQ / Townsquare Media, Inc. / Madison Square Garden Entertainment Corp. - SC 13D/A Activist Investment

SC 13D/A 1 d539682dsc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 3 – Exit Filing)* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 892231-10-1 (CUSIP Number) Philip D’Ambrosio Executive Vice President & Treasurer

STOCK REPURCHASE AGREEMENT

EX-99.2 2 d539682dex992.htm EX-99.2 Exhibit 2 STOCK REPURCHASE AGREEMENT THIS STOCK REPURCHASE AGREEMENT (this “Agreement”) is entered into as of April 1, 2024 by and among Townsquare Media, Inc., a Delaware corporation (the “Company”), and the legal entity set forth on Schedule A (the “Seller”). RECITALS WHEREAS, as of the date hereof, the Seller holds 1,708,139 shares (the “Class A Shares”) of t

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): April 1, 2024 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organization

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES REPURCHASE OF JUST UNDER 10% OF OUTSTANDING SHARES REAFFIRMS Q1’24 AND FY’24 GUIDANCE Purchase, NY – April 1, 2024 - Townsquare Media, Inc. (NYSE: TSQ) (the “Company” or “Townsquare”) announced that today we are

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES REPURCHASE OF JUST UNDER 10% OF OUTSTANDING SHARES REAFFIRMS Q1’24 AND FY’24 GUIDANCE Purchase, NY – April 1, 2024 - Townsquare Media, Inc.

SCHEDULE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Definitive Proxy State

SCHEDULE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) x Definitive Proxy State

TOWNSQUARE ANNOUNCES FOURTH QUARTER AND FULL YEAR 2023 RESULTS ANNOUNCES INCREASE IN DIVIDEND Digital Growth and Strong Profit Margins Across Segments Contribute to Strong Cash Flow Growth: Generated $68 Million of Cash Flow from Operations, +35% Yea

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES FOURTH QUARTER AND FULL YEAR 2023 RESULTS ANNOUNCES INCREASE IN DIVIDEND Digital Growth and Strong Profit Margins Across Segments Contribute to Strong Cash Flow Growth: Generated $68 Million of Cash Flow from Operations, +35% Year-over-Year Purchase, NY – March 15, 2024 - Townsquare Media, Inc.

Clawback Policy, adopted as of October 26, 2023.

clawbackpolicy10262023 CLAWBACK POLICY TOWNSQUARE MEDIA, INC. PURPOSE Townsquare Media, Inc. (the “Company”) believes that it is in the best interests of the Company and its shareholders to create and maintain a culture that emphasizes integrity and accountability and that reinforces the Company’s pay-for-performance compensation philosophy. The Company’s Board of Directors (the “Board”) has there

List of Subsidiaries of Townsquare Media, Inc.

Exhibit 21.1 Subsidiaries of Townsquare Media, Inc. Exact Name of Subsidiaries of Registrant Jurisdiction of Incorporation or Organization Townsquare Live Events International, LLC Delaware Townsquare Next, LLC Delaware Townsquare Live Productions, LLC Delaware Townsquare Interactive, LLC Delaware Townsquare MMN, LLC Delaware Townsquare Commerce, LLC Delaware Townsquare Finance, LLC Delaware Towns

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): March 15, 2024 Townsquare Media,

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): March 15, 2024 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizatio

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc. (Ex

Description of Securities Registered Pursuant to Section 12 of the Exchange Act of 1934

Exhibit 4.6 DESCRIPTION OF SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 The Class A common stock, par value $0.01 per share, of Townsquare Media, Inc. (“Townsquare”, “the Company”, “we”, “our” and “us”) is the only class of securities of Townsquare registered under Section 12 of the Securities Exchange Act of 1934, as amended. The following summary of certain

TSQ / Townsquare Media, Inc. / Madison Square Garden Entertainment Corp. - SC 13D/A Activist Investment

SC 13D/A CONFIDENTIAL UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

TSQ / Townsquare Media, Inc. / AMERICAN CENTURY INVESTMENT MANAGEMENT INC - SC 13G/A Passive Investment

SC 13G/A 1 townsquaremedia13g-a4.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 4) * TOWNSQUARE MEDIA, INC. (Name of Issuer) CLASS A COMMON STOCK (Title of Class of Securities) 892231101 (CUSIP Number) DECEMBER 31, 2023 (Date of Event Which Requires Filing of this Statement) Check the approp

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): December 21, 2023 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation) (Commissio

First Amendment, dated as of December 21, 2023, to the Amended and Restated Employment Agreement, dated as of October 7, 2022, by and between Townsquare Media, Inc. and Erik Hellum.

FIRST AMENDMENT TO THE AMENDED AND RESTATED EMPLOYMENT AGREEMENT THIS FIRST AMENDMENT TO THE AMENDED AND RESTATED EMPLOYMENT AGREEMENT (this “Amendment”) is entered into as of December 21, 2023 (the “Effective Date”), by and between Townsquare Media, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 ☐ TRANSITION REPORT PURSUANT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media,

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): November 9, 2023 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizat

TOWNSQUARE ANNOUNCES THIRD QUARTER RESULTS September YTD Net Revenue Excluding Political Flat Year-Over-Year Digital Represents 52% of September YTD 2023 Total Net Revenue and 57% of September YTD 2023 Total Adjusted Operating Income

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES THIRD QUARTER RESULTS September YTD Net Revenue Excluding Political Flat Year-Over-Year Digital Represents 52% of September YTD 2023 Total Net Revenue and 57% of September YTD 2023 Total Adjusted Operating Income Purchase, NY – November 9, 2023 - Townsquare Media, Inc.

TOWNSQUARE ANNOUNCES SECOND QUARTER RESULTS THAT DEMONSTRATE ONGOING DIGITAL ADVERTISING STRENGTH Q2 Digital Advertising Net Revenue Increased 11% YOY Digital Represents 52% of 1H 2023 Total Net Revenue and 60% of 1H 2023 Total Adjusted Operating Inc

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES SECOND QUARTER RESULTS THAT DEMONSTRATE ONGOING DIGITAL ADVERTISING STRENGTH Q2 Digital Advertising Net Revenue Increased 11% YOY Digital Represents 52% of 1H 2023 Total Net Revenue and 60% of 1H 2023 Total Adjusted Operating Income Purchase, NY – August 9, 2023 - Townsquare Media, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 ☐ TRANSITION REPORT PURSUANT TO S

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): August 9, 2023 Townsquare Media,

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): August 9, 2023 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizatio

STOCK REPURCHASE AGREEMENT

EX-99.2 Exhibit 2 STOCK REPURCHASE AGREEMENT THIS STOCK REPURCHASE AGREEMENT (this “Agreement”) is entered into as of June 15, 2023 by and among Townsquare Media, Inc., a Delaware corporation (the “Company”), and the legal entity set forth on Schedule A (the “Seller”). RECITALS WHEREAS, as of the date hereof, the Seller holds (i) 583,139 shares (the “Class A Shares”) of the Company’s Class A Commo

TSQ / Townsquare Media Inc - Class A / Madison Square Garden Entertainment Corp. - SC 13D/A Activist Investment

SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 892231-10-1 (CUSIP Number) Philip D’Ambrosio Executive Vice President & Treasurer Madison Square Garden Entertainment Corp. Tw

JOINT FILING AGREEMENT

EX-99.1 Exhibit 1 JOINT FILING AGREEMENT This will confirm the agreement by and among all the undersigned that the Schedule 13D filed on or about this date and any amendments thereto with respect to the beneficial ownership by the undersigned of the Class A Common Stock, par value $0.01 per share, of Townsquare Media, Inc. is being filed on behalf of each of the undersigned in accordance with Rule

TOWNSQUARE ANNOUNCES SIGNIFICANT SHARE REPURCHASE

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES SIGNIFICANT SHARE REPURCHASE Purchase, NY – June 16, 2023 - Townsquare Media, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 16, 2023 Townsquare Media, I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 16, 2023 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organization

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 12, 2023 (May 10, 2023) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation o

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 ☐ TRANSITION REPORT PURSUANT TO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): May 10, 2023 Townsquare Media, In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): May 10, 2023 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organization)

TOWNSQUARE ANNOUNCES FIRST QUARTER RESULTS WHICH DEMONSTRATE ONGOING STRENGTH OF ITS DIGITAL FIRST STRATEGY Q1 Digital Advertising Net Revenue Increased 15.4% YOY Digital Revenue Represents 54% of Q1 Total Net Revenue

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES FIRST QUARTER RESULTS WHICH DEMONSTRATE ONGOING STRENGTH OF ITS DIGITAL FIRST STRATEGY Q1 Digital Advertising Net Revenue Increased 15.

JOINT FILING AGREEMENT

EX-99.1 Exhibit 1 JOINT FILING AGREEMENT This will confirm the agreement by and among all the undersigned that the Schedule 13D filed on or about this date and any amendments thereto with respect to the beneficial ownership by the undersigned of the Class A Common Stock, par value $0.01 per share, of Townsquare Media, Inc. is being filed on behalf of each of the undersigned in accordance with Rule

TSQ / Townsquare Media Inc - Class A / Madison Square Garden Entertainment Corp. - SC 13D Activist Investment

SC 13D UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 892231-10-1 (CUSIP Number) David F. Byrnes Executive Vice President and Chief Financial Officer Madison Square Garden Entertainme

JOINT FILING AGREEMENT

EX-99.1 Exhibit 1 JOINT FILING AGREEMENT This will confirm the agreement by and among all the undersigned that the Schedule 13D filed on or about this date and any amendments thereto with respect to the beneficial ownership by the undersigned of the Class A Common Stock, par value $0.01 per share, of Townsquare Media, Inc. is being filed on behalf of each of the undersigned in accordance with Rule

TSQ / Townsquare Media Inc - Class A / Madison Square Garden Entertainment Corp. - SC 13D/A Activist Investment

SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 2)* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 892231-10-1 (CUSIP Number) Gautam Ranji Executive Vice President, Chief Financial Officer and Treasurer Sphere Entertainment C

SCHEDULE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Definitive Proxy State

SCHEDULE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) x Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc. (Ex

List of Subsidiaries of Townsquare Media, Inc.

Exhibit 21.1 Subsidiaries of Townsquare Media, Inc. Exact Name of Subsidiaries of Registrant Jurisdiction of Incorporation or Organization Townsquare Live Events International, LLC Delaware Townsquare Next, LLC Delaware Townsquare Live Productions, LLC Delaware Townsquare Interactive, LLC Delaware Townsquare MMN, LLC Delaware Townsquare Commerce, LLC Delaware Townsquare Finance, LLC Delaware Towns

Description of Securities Registered Pursuant to Section 12 of the Exchange Act of 1934

Exhibit 4.6 DESCRIPTION OF SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 The Class A common stock, par value $0.01 per share, of Townsquare Media, Inc. (“Townsquare”, “the Company”, “we”, “our” and “us”) is the only class of securities of Townsquare registered under Section 12 of the Securities Exchange Act of 1934, as amended. The following summary of certain

TOWNSQUARE REPORTS ALL-TIME HIGH NET REVENUE AND ADJUSTED EBITDA IN 2022 Digital Transformation Evident: 50% of Total Revenue and Adjusted Operating Income from Digital Sources in 2022, as Digital Revenue Increases +16% YOY Net Leverage Declines to A

IMMEDIATE RELEASE TOWNSQUARE REPORTS ALL-TIME HIGH NET REVENUE AND ADJUSTED EBITDA IN 2022 Digital Transformation Evident: 50% of Total Revenue and Adjusted Operating Income from Digital Sources in 2022, as Digital Revenue Increases +16% YOY Net Leverage Declines to All-Time Low 4.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): March 9, 2023 Townsquare Media, I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): March 9, 2023 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organization

TSQ / Townsquare Media Inc / MSD CAPITAL L P - SC 13G/A Passive Investment

SC 13G/A CUSIP No. 892231101 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 2)* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 892231101 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to desig

AGREEMENT REGARDING THE JOINT FILING OF SCHEDULE 13G

EX-99.1 CUSIP No. 892231101 Exhibit 99.1 AGREEMENT REGARDING THE JOINT FILING OF SCHEDULE 13G The undersigned hereby agree as follows: (i) Each of them is individually eligible to use the Schedule 13G to which this Exhibit is attached, and such Schedule 13G is filed on behalf of each of them; and (ii) Each of them is responsible for the timely filing of such Schedule 13G and any amendments thereto

TSQ / Townsquare Media Inc / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1 )* Townsquare Media Inc (Name of Issuer) Common Stock (Title of Class of Securities) 892231101 (CUSIP Number) December 30, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this S

TSQ / Townsquare Media Inc / AMERICAN CENTURY INVESTMENT MANAGEMENT INC - SC 13G/A Passive Investment

United States Securities and Exchange Commission Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 3)* TOWNSQUARE MEDIA, INC. (Name of Issuer) CLASS A COMMON STOCK (Title of Class of Securities) 892231101 (CUSIP Number) DECEMBER 31, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to whi

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): December 22, 2022 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organiza

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): November 9, 2022 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizat

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 ☐ TRANSITION REPORT PURSUANT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media,

TOWNSQUARE SETS THIRD QUARTER RECORD BY ACHIEVING ALL-TIME Q3 HIGH FOR BOTH NET REVENUE (+8% YEAR-OVER-YEAR) AND ADJUSTED EBITDA (+6% YEAR-OVER-YEAR) Digital Transformation Evident with Digital Revenue Growth of +17% YOY in Q3 and September YTD 2022

IMMEDIATE RELEASE TOWNSQUARE SETS THIRD QUARTER RECORD BY ACHIEVING ALL-TIME Q3 HIGH FOR BOTH NET REVENUE (+8% YEAR-OVER-YEAR) AND ADJUSTED EBITDA (+6% YEAR-OVER-YEAR) Digital Transformation Evident with Digital Revenue Growth of +17% YOY in Q3 and September YTD 2022 Digital Revenue and Adjusted Operating Income ~50% of Total Net Leverage Declined to All-Time Low 4.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No.1) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 ☐ TRANSITION REPOR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No.1) ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsqu

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q/A (Amendment No.1) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 ☐ TRANSITION

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q/A (Amendment No.1) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 To

Amended and Restated Employment Agreement, dated, October 7, 2022, by and between Townsquare Media Inc. and Bill Wilson.

? Exhibit?10.1 ? AMENDED AND RESTATED EMPLOYMENT AGREEMENT ? THIS AMENDED AND RESTATED EMPLOYMENT AGREEMENT (the ?Agreement?) is entered into as of October?7, 2022, by and between Townsquare Media,?Inc., a Delaware corporation (the ?Company?), and Bill Wilson (?Executive?). ? RECITALS ? WHEREAS, Executive and the Company are party to that certain Employment Agreement, dated as of October?16, 2017,

Amended and Restated Employment Agreement, dated, October 7, 2022, by and between Townsquare Media Inc. and Stuart Rosenstein.

Exhibit 10.2 AMENDED AND RESTATED EMPLOYMENT AGREEMENT THIS AMENDED AND RESTATED EMPLOYMENT AGREEMENT (the ?Agreement?) is entered into as of October 7, 2022, by and between Townsquare Media, Inc., a Delaware corporation (the ?Company?), and Stuart Rosenstein (?Executive?). RECITALS WHEREAS, Executive and the Company are party to that certain Employment Agreement, dated as of October 16, 2017, as

Amended and Restated Employment Agreement, dated, October 7, 2022, by and between Townsquare Media Inc. and Erik Hellum.

? Exhibit?10.3 ? AMENDED AND RESTATED EMPLOYMENT AGREEMENT ? THIS AMENDED AND RESTATED EMPLOYMENT AGREEMENT (the ?Agreement?) is entered into as of October?7, 2022, by and between Townsquare Media,?Inc., a Delaware corporation (the ?Company?), and Erik Hellum (?Executive?). ? RECITALS ? WHEREAS, Executive and the Company are party to that certain Employment Agreement, dated as of October?25, 2017,

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 7, 2022 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of (Commission File Number) (I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 ☐ TRANSITION REPORT PURSUANT TO S

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc.

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): August 9, 2022 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizatio

TOWNSQUARE’S SECOND QUARTER NET REVENUE AND ADJUSTED EBITDA REACH ALL-TIME HIGH WITH NET REVENUE +14% AND ADJUSTED EBITDA +7% YEAR-OVER-YEAR June YTD 2022 Digital Revenue and Adjusted Operating Income 50% of Total Net Leverage Declines to 4.65x Raisi

IMMEDIATE RELEASE TOWNSQUARE?S SECOND QUARTER NET REVENUE AND ADJUSTED EBITDA REACH ALL-TIME HIGH WITH NET REVENUE +14% AND ADJUSTED EBITDA +7% YEAR-OVER-YEAR June YTD 2022 Digital Revenue and Adjusted Operating Income 50% of Total Net Leverage Declines to 4.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): August 2, 2022 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizatio

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): May 13, 2022 (May 10, 2022) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation o

TOWNSQUARE’S FIRST QUARTER NET REVENUE AND ADJUSTED EBITDA SET Q1 RECORD WITH NET REVENUE +13% AND ADJUSTED EBITDA +10% YEAR-OVER-YEAR Q1 2022 Digital Revenue Grows +16% YOY - Now 51% of Total Net Revenue Q1 2022 Digital Adjusted Operating Income is

IMMEDIATE RELEASE TOWNSQUARE?S FIRST QUARTER NET REVENUE AND ADJUSTED EBITDA SET Q1 RECORD WITH NET REVENUE +13% AND ADJUSTED EBITDA +10% YEAR-OVER-YEAR Q1 2022 Digital Revenue Grows +16% YOY - Now 51% of Total Net Revenue Q1 2022 Digital Adjusted Operating Income is 55% of Total Net Leverage Declines to 4.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): May 10, 2022 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organization)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 ☐ TRANSITION REPORT PURSUANT TO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc

SCHEDULE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) x Definitive Proxy State

SCHEDULE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 ☐ TRANSITION REPORT PURSUANT TO SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc. (Ex

Description of Securities Registered Pursuant to Section 12 of the Exchange Act of 1934

Exhibit 4.6 DESCRIPTION OF SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 The Class A common stock, par value $0.01 per share, of Townsquare Media, Inc. (?Townsquare?, ?the Company?, ?we?, ?our? and ?us?) is the only class of securities of Townsquare registered under Section 12 of the Securities Exchange Act of 1934, as amended. The following summary of certain

2021 Employee Stock Purchase Plan

Exhibit 10.7.7 TOWNSQUARE MEDIA, INC. 2021 EMPLOYEE STOCK PURCHASE PLAN ARTICLE I PURPOSE AND SCOPE OF THE PLAN 1.1 Purpose and Scope. The purpose of the Townsquare Media, Inc. 2021 Employee Stock Purchase Plan, as it may be amended from time to time, (the ?Plan?) is to assist service providers of Townsquare Media, Inc., a Delaware corporation (the ?Company?), and its Subsidiaries in acquiring a s

List of Subsidiaries of Townsquare Media, Inc.

Exhibit 21.1 Subsidiaries of Townsquare Media, Inc. Exact Name of Subsidiaries of Registrant Jurisdiction of Incorporation or Organization Townsquare Live Events International, LLC Delaware Townsquare Next, LLC Delaware Townsquare Live Productions, LLC Delaware Townsquare Interactive, LLC Delaware Townsquare MMN, LLC Delaware Townsquare Commerce, LLC Delaware Townsquare Finance, LLC Delaware Towns

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): March 10, 2022 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizatio

TOWNSQUARE REPORTS ALL-TIME HIGH ADJUSTED EBITDA OF $105M IN 2021 (103% of 2019) AND STRONG DOUBLE-DIGIT NET REVENUE GROWTH OF +13% (99.8% of 2019 Excluding Live Events) 2021 Digital Revenue Increased +19% to $199M, Accounting for 48% of Total Net Re

IMMEDIATE RELEASE TOWNSQUARE REPORTS ALL-TIME HIGH ADJUSTED EBITDA OF $105M IN 2021 (103% of 2019) AND STRONG DOUBLE-DIGIT NET REVENUE GROWTH OF +13% (99.

TSQ / Townsquare Media Inc / MSD CAPITAL L P Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to 240.13d-2 UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 892231101 (CUSIP Number)

TSQ / Townsquare Media Inc / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Townsquare Media Inc (Name of Issuer) Common Stock (Title of Class of Securities) 892231101 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Sch

TSQ / Townsquare Media Inc / AMERICAN CENTURY INVESTMENT MANAGEMENT INC - SC 13G/A Passive Investment

United States Securities and Exchange Commission Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2)* TOWNSQUARE MEDIA, INC. (Name of Issuer) CLASS A COMMON STOCK (Title of Class of Securities) 892231101 (CUSIP Number) DECEMBER 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to whi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 ☐ TRANSITION REPORT PURSUANT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media,

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): November 2, 2021 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizat

TOWNSQUARE REPORTS STRONG THIRD QUARTER NET REVENUE (99% of Q3 2019) AND ADJUSTED EBITDA (104% of Q3 2019) Adjusted EBITDA Exceeds 2019 Levels for the Fourth Consecutive Quarter Digital Revenue 47% of Total Net Revenue (Excluding Political) in YTD 20

IMMEDIATE RELEASE TOWNSQUARE REPORTS STRONG THIRD QUARTER NET REVENUE (99% of Q3 2019) AND ADJUSTED EBITDA (104% of Q3 2019) Adjusted EBITDA Exceeds 2019 Levels for the Fourth Consecutive Quarter Digital Revenue 47% of Total Net Revenue (Excluding Political) in YTD 2021 Raising 2021 Guidance Purchase, NY ? November 2, 2021 - Townsquare Media, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 ☐ TRANSITION REPORT PURSUANT TO S

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc.

TOWNSQUARE REPORTS AN ALL-TIME RECORD ADJUSTED EBITDA AND STRONG NET REVENUE GROWTH Adjusted EBITDA Exceeds 2019 Levels for the Third Consecutive Quarter Delivers Record High Townsquare Interactive Net Subscriber Adds (+1,350 in Q2) Digital Revenue 4

IMMEDIATE RELEASE TOWNSQUARE REPORTS AN ALL-TIME RECORD ADJUSTED EBITDA AND STRONG NET REVENUE GROWTH Adjusted EBITDA Exceeds 2019 Levels for the Third Consecutive Quarter Delivers Record High Townsquare Interactive Net Subscriber Adds (+1,350 in Q2) Digital Revenue 47% of Total Net Revenue in 1H 2021 Purchase, NY ? August 3, 2021 - Townsquare Media, Inc.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): August 3, 2021 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizatio

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): May 14, 2021 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organization)

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): May 14, 2021 (May 11, 2021) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation o

Letter Agreement (Exhibit 2 of the Amendment No.1 to the Schedule 13D in respect of Townsquare Media, Inc. filed by Sphere Entertainment Co. (formerly Madison Square Garden Entertainment Corp.)) †

Exhibit 2 Exhibit 2 MSG National Properties, LLC c/o Madison Square Garden Entertainment Corp.

Joint Filing Agreement, by and among the Reporting Persons, dated May 13, 2021.*

Exhibit 1 Exhibit 1 JOINT FILING AGREEMENT This will confirm the agreement by and among all the undersigned that the Schedule 13D filed on or about this date and any amendments thereto with respect to the beneficial ownership by the undersigned of the Class A Common Stock, par value $0.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class

SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 892231-10-1 (CUSIP Number) Mark H. FitzPatrick Executive Vice President and Chief Financial Officer Madison Square Garden Ente

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): May 10, 2021 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organization)

TOWNSQUARE REPORTS STRONG START TO 2021 WITH DIGITAL REVENUE, GROWING +13% YEAR OVER YEAR (+32% vs. 2019) AND ADJUSTED EBITDA GROWING +30% YEAR OVER YEAR (+7% vs. 2019) Digital Revenue Nearly 49% of Total Net Revenue

IMMEDIATE RELEASE TOWNSQUARE REPORTS STRONG START TO 2021 WITH DIGITAL REVENUE, GROWING +13% YEAR OVER YEAR (+32% vs.

- DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) x Definitive Proxy State

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Definitive Proxy State

List of Subsidiaries of Townsquare Media, Inc.

Subsidiaries of Townsquare Media, Inc. Exact Name of Subsidiaries of Registrant Jurisdiction of Incorporation or Organization Townsquare Live Events International, LLC Delaware Townsquare Next, LLC Delaware Townsquare Live Productions, LLC Delaware Townsquare Interactive, LLC Delaware Townsquare MMN, LLC Delaware Townsquare Commerce, LLC Delaware Townsquare Finance, LLC Delaware Townsquare Managem

TOWNSQUARE REPORTS STRONG CONCLUSION TO 2020 POWERED BY DIGITAL REVENUE, GROWING +6% YEAR OVER YEAR TO $162 MILLION AND REPRESENTING 44% OF TOTAL 2020 NET REVENUE Q4 2020 Adjusted EBITDA +8.4% Townsquare Interactive 2020 Net Subscription Revenue Incr

IMMEDIATE RELEASE TOWNSQUARE REPORTS STRONG CONCLUSION TO 2020 POWERED BY DIGITAL REVENUE, GROWING +6% YEAR OVER YEAR TO $162 MILLION AND REPRESENTING 44% OF TOTAL 2020 NET REVENUE Q4 2020 Adjusted EBITDA +8.

Description of Securities Registered Pursuant to Section 12 of the Exchange Act of 1934

DESCRIPTION OF SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 The Class A common stock, par value $0.

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc. (Ex

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): March 16, 2021 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizatio

JOINT FILING AGREEMENT OCM POF IV AIF GAP HOLDINGS, L.P. OCM PF/FF RADIO HOLDINGS PT, L.P. OCM/GAP HOLDINGS IV, LLC OCM PRINCIPAL OPPORTUNITIES FUND IV AIF (DELAWARE), L.P. OAKTREE FUND AIF SERIES, L.P. – SERIES I, SERIES D AND SERIES B OAKTREE FUND

tsq-jointfilingagreement JOINT FILING AGREEMENT OCM POF IV AIF GAP HOLDINGS, L.P. OCM PF/FF RADIO HOLDINGS PT, L.P. OCM/GAP HOLDINGS IV, LLC OCM PRINCIPAL OPPORTUNITIES FUND IV AIF (DELAWARE), L.P. OAKTREE FUND AIF SERIES, L.P. – SERIES I, SERIES D AND SERIES B OAKTREE FUND GP AIF, LLC OAKTREE FUND GP III, L.P. OAKTREE AIF INVESTMENTS, L.P. OAKTREE AIF INVESTMENT GP LLC ATLAS OCM HOLDINGS, LLC OAK

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 3)* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 3)* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 892231101 (CUSIP Number) Todd E. Molz Managing Director and General Counsel Oaktree Capital Group Holdings GP, LLC 333 South Grand Aven

Settlement Agreement, dated as of March 8, 2021, by and among Townsquare Media, Inc., OCM POF IV AIF GAP Holdings, L.P., OCM PF/FF Radio Holdings PT, L.P., Oaktree FF Investment Fund, L.P., Second Street Holdings 1, L.P., Second Street Holdings 2, L.P., Second Street Holdings 3, L.P., Second Street Holdings 4, L.P., Second Street Holdings 5, L.P., Second Street Holdings 6, L.P., Second Street Holdings 7, L.P., and Second Street Holdings 8, L.P

SETTLEMENT AGREEMENT This Settlement Agreement (this ?Agreement?), dated as of March 8, 2021 (the ?Effective Date?), is made between and among Townsquare Media, Inc.

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): March 8, 2021 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organization

- DEF 14C

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14C INFORMATION Information Statement Pursuant to Section 14(c) of the Securities Exchange Act of 1934 Check the appropriate box: ? Preliminary Information Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14c-5(d)(2)) ? Definitive Information Statement TOWNSQUARE MEDIA, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1) Townsquare Media, Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 892231101 (CUSIP Number) Jonathan Brolin Edenbrook Capital, LLC 116 Radio Circle Mount Kisco, NY 10549 (914) 239-3117 (Name, Address and

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): February 15, 2021 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organiza

United States Securities and Exchange Commission Washington, D.C. 20549

United States Securities and Exchange Commission Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* TOWNSQUARE MEDIA, INC. (Name of Issuer) CLASS A COMMON STOCK (Title of Class of Securities) 892231101 (CUSIP Number) DECEMBER 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to whi

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 2)* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 2)* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 892231101 (CUSIP Number) Todd E. Molz Managing Director and General Counsel Oaktree Capital Group Holdings GP, LLC 333 South Grand Aven

JOINT FILING AGREEMENT OCM POF IV AIF GAP HOLDINGS, L.P. OCM PF/FF RADIO HOLDINGS PT, L.P. OCM/GAP HOLDINGS IV, LLC OCM PRINCIPAL OPPORTUNITIES FUND IV AIF (DELAWARE), L.P. OAKTREE FUND AIF SERIES, L.P. – SERIES I, SERIES D AND SERIES B OAKTREE FUND

jointfilingagreement JOINT FILING AGREEMENT OCM POF IV AIF GAP HOLDINGS, L.P. OCM PF/FF RADIO HOLDINGS PT, L.P. OCM/GAP HOLDINGS IV, LLC OCM PRINCIPAL OPPORTUNITIES FUND IV AIF (DELAWARE), L.P. OAKTREE FUND AIF SERIES, L.P. – SERIES I, SERIES D AND SERIES B OAKTREE FUND GP AIF, LLC OAKTREE FUND GP III, L.P. OAKTREE AIF INVESTMENTS, L.P. OAKTREE AIF INVESTMENT GP LLC ATLAS OCM HOLDINGS, LLC OAKTREE

TOWNSQUARE ANNOUNCES SIGNIFICANT SHARE REPURCHASE OF A MINIMUM OF 10 MILLION SHARES

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES SIGNIFICANT SHARE REPURCHASE OF A MINIMUM OF 10 MILLION SHARES Purchase, NY - January 25, 2021 - Townsquare Media, Inc.

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of report (Date of earliest event reported): January 24, 2021 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organizat

Stock Repurchase Agreement dated January 24, 2021 by and between Townsquare Media, Inc. and certain affiliates of Oaktree Capital Management L.P

tsq-stockrepurchaseagree

Amendment to 2014 Omnibus Incentive Plan

AMENDMENT TO THE TOWNSQUARE MEDIA, INC. 2014 OMNIBUS INCENTIVE PLAN January 27, 2021 This Amendment (this “Amendment”) to the Townsquare Media, Inc. 2014 Omnibus Incentive Plan (the “Plan”), dated as of January 27, 2021, has been approved by the board of directors and the holders of a majority of the issued and outstanding shares of Townsquare Media, Inc., a Delaware corporation (the “Company”). A

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): January 19, 2021 Commission file number 001-36558 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 27-1996555 (State or other jurisdiction of inc

Indenture, dated as of January 6, 2021, among the Company, the guarantors named therein and Wilmington Trust, National Association, as trustee and notes collateral agent.

tsq-indenture Execution Version Table of Contents provided plus plus over provided however provided provided provided plus plus plus plus plus plus pro- vided plus plus provided plus plus plus plus plus plus plus plus plus plus plus plus plus less provided however minus provided provided however provided provided however provided however provided provided further provided however provided further

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Termination of a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): January 6, 2021 Commission file number 001-36558 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 27-1996555 (State or other jurisdiction of inco

TOWNSQUARE MEDIA ANNOUNCES PRICING OF $550 MILLION SENIOR SECURED NOTES OFFERING

IMMEDIATE RELEASE TOWNSQUARE MEDIA ANNOUNCES PRICING OF $550 MILLION SENIOR SECURED NOTES OFFERING Purchase, NY - December 16, 2020 - Townsquare Media, Inc.

Financial Statements and Exhibits, Other Events - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 16, 2020 Commission file number 001-36558 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 27-1996555 (State or other jurisdiction of in

TOWNSQUARE MEDIA, INC. REPORTS PRELIMINARY ESTIMATED FOURTH QUARTER 2020 RESULTS

IMMEDIATE RELEASE TOWNSQUARE MEDIA, INC. REPORTS PRELIMINARY ESTIMATED FOURTH QUARTER 2020 RESULTS Purchase, NY - December 15, 2020 - Townsquare Media, Inc. (NYSE: TSQ) (“Townsquare”, the "Company," "we," "us," or "our") announced today preliminary estimated financial results for the fourth quarter and full year ended December 31, 2020. “We are pleased to pre-announce very strong fourth quarter es

TOWNSQUARE MEDIA ANNOUNCES LAUNCH OF $550 MILLION SENIOR SECURED NOTES OFFERING

IMMEDIATE RELEASE TOWNSQUARE MEDIA ANNOUNCES LAUNCH OF $550 MILLION SENIOR SECURED NOTES OFFERING Purchase, NY - December 15, 2020 - Townsquare Media, Inc.

Regulation FD Disclosure, Financial Statements and Exhibits, Other Events - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 15, 2020 Commission file number 001-36558 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 27-1996555 (State or other jurisdiction of in

TSQ / Townsquare Media, Inc. / Madison Square Garden Entertainment Corp. - SC 13D Activist Investment

SC 13D UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* Townsquare Media, Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 892231-10-1 (CUSIP Number) Mark H. FitzPatrick Executive Vice President and Chief Financial Officer Madison Square Garden Enterta

JOINT FILING AGREEMENT

Exhibit 1 Exhibit 1 JOINT FILING AGREEMENT This will confirm the agreement by and among all the undersigned that the Schedule 13D filed on or about this date and any amendments thereto with respect to the beneficial ownership by the undersigned of the Class A Common Stock, par value $0.

Joinder to the Registration Agreement (Exhibit 6 to the Schedule 13D in respect of Townsquare Media, Inc. filed by Sphere Entertainment Co. (formerly Madison Square Garden Entertainment Corp.)) †

Exhibit 6 Exhibit 6 JOINDER REGISTRATION AGREEMENT This JOINDER (the “Joinder”) to the Registration Agreement, dated as of August 16, 2016, by and between Townsquare Media, Inc.

TOWNSQUARE REPORTS STRONG IMPROVEMENT IN Q3 2020 POWERED BY DIGITAL REVENUE, GROWING +7% YEAR OVER YEAR AND REPRESENTING 44% OF TOTAL Q3 NET REVENUE Townsquare Interactive Q3 Net Subscription Revenue Increased 14.5% 1,150 Q3 Net Subscriber Additions

IMMEDIATE RELEASE TOWNSQUARE REPORTS STRONG IMPROVEMENT IN Q3 2020 POWERED BY DIGITAL REVENUE, GROWING +7% YEAR OVER YEAR AND REPRESENTING 44% OF TOTAL Q3 NET REVENUE Townsquare Interactive Q3 Net Subscription Revenue Increased 14.

Financial Statements and Exhibits, Results of Operations and Financial Condition - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 9, 2020 Commission file number 001-36558 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 27-1996555 (State or other jurisdiction of inc

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsq

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): September 21, 2020 Commission fil

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): September 21, 2020 Commission file number 001-36558 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 27-1996555 (State or other jurisdiction of i

TSQ / Townsquare Media, Inc. / Edenbrook Capital, LLC - FORM SC 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. ) TOWNSQUARE MEDIA, INC. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 892231101 (CUSIP Number) Jonathan Brolin Edenbrook Capital, LLC 116 Radio Circle Mount Kisco, NY 10549 (914) 239-3117 (Name, Address and

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 12, 2020 (August 6, 2020) Commission file number 001-36558 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 27-1996555 (State or other jur

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 10, 2020 Commission file number 001-36558 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 27-1996555 (State or other jurisdiction of inco

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2020 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare

TOWNSQUARE ANNOUNCES SECOND QUARTER RESULTS Townsquare Interactive Q2 Net Revenue Increased 10.5% 9th Consecutive Quarter of 850 (or more) Net Subscriber Additions at Townsquare Interactive Digital Revenue over 48% of Total Net Revenue

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES SECOND QUARTER RESULTS Townsquare Interactive Q2 Net Revenue Increased 10.

2020 Proxy Statement

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) x Definitive Proxy State

Annual Report - 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A Amendment No. 1 ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2019 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsqua

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2020 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 15, 2020 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36558 (Commissi

TOWNSQUARE ANNOUNCES FIRST QUARTER 2020 RESULTS 9th Consecutive Quarter of Pro Forma Net Revenue Growth Digital Revenue over 40% of Total Net Revenue

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES FIRST QUARTER 2020 RESULTS 9th Consecutive Quarter of Pro Forma Net Revenue Growth Digital Revenue over 40% of Total Net Revenue Purchase, NY - June 15, 2020 - Townsquare Media, Inc.

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2019 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc. (Ex

List of Subsidiaries of Townsquare Media, Inc.

Subsidiaries of Townsquare Media, Inc. Exact Name of Subsidiaries of Registrant Jurisdiction of Incorporation or Organization Townsquare Live Events International, LLC Delaware Townsquare Next, LLC Delaware Townsquare Live Productions, LLC Delaware Townsquare Interactive, LLC Delaware Townsquare MMN, LLC Delaware Townsquare Commerce, LLC Delaware Townsquare Finance, LLC Delaware Townsquare Managem

Material Impairments, Non-Reliance on Previously Issued Financial Statements or a Related Audit Report or Completed Interim Review

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 3, 2020 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36558 (Commissio

Description of Securities Registered Pursuant to Section 12 of the Exchange Act of 1934

DESCRIPTION OF SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 The Class A common stock, par value $0.

TOWNSQUARE ANNOUNCES CONFERENCE CALL TO DISCUSS FIRST QUARTER 2020 RESULTS

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES CONFERENCE CALL TO DISCUSS FIRST QUARTER 2020 RESULTS Purchase, NY - May 11, 2020 - Townsquare Media, Inc.

Regulation FD Disclosure, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 11, 2020 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36558 (Commissio

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 17, 2020 (April 13, 2020) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 0

Amendment No. 5, dated April 13, 2020, to the Credit Agreement, dated as of April 1, 2015, as amended, among Townsquare Media, Inc., each lender from time to time party thereto, and Royal Bank of Canada, as administrative agent and collateral agent (incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K filed on April 17, 2020)

EXECUTION VERSION AMENDMENT NO. 5 AMENDMENT NO. 5, dated as of April 13, 2020 (this “Amendment”), to the Credit Agreement, dated as of April 1, 2015 (as amended by the Incremental Amendment Agreement No. 1 dated as of September 1, 2015, Amendment No. 2 dated as of February 8, 2017, Amendment No. 3 dated as of October 20, 2017, Amendment No. 4 dated as of April 30, 2019 and as further amended, supp

Regulation FD Disclosure, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 2, 2020 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36558 (Commissi

TOWNSQUARE MEDIA PROVIDES UPDATED ON FORM 10-K FILING

IMMEDIATE RELEASE TOWNSQUARE MEDIA PROVIDES UPDATED ON FORM 10-K FILING Purchase, NY - April 8, 2020 - Townsquare Media, Inc.

Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 20, 2020 (March 17, 2020) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 0

TOWNSQUARE ANNOUNCES STRONG 2019 NET REVENUE GROWTH OF 8% (EX POLITICAL) AND ADJUSTED EBITDA GROWTH OF 15% (EX POLITICAL) 2019 Digital Revenue Increased More Than 25% to over $150 Million 4.6x Net Leverage*

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES STRONG 2019 NET REVENUE GROWTH OF 8% (EX POLITICAL) AND ADJUSTED EBITDA GROWTH OF 15% (EX POLITICAL) 2019 Digital Revenue Increased More Than 25% to over $150 Million 4.

TSQ / Townsquare Media, Inc. NT 10-K - - NT 10-K

SEC FILE NUMBER 001-36558 CUSIP NUMBER 892231 101 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 16, 2020 (December 31, 2019) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization

TSQ / Townsquare Media, Inc. / AMERICAN CENTURY INVESTMENT MANAGEMENT INC - SC 13G Passive Investment

United States Securities and Exchange Commission Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* TOWNSQUARE MEDIA, INC. (Name of Issuer) CLASS A COMMON STOCK (Title of Class of Securities) 892231101 (CUSIP Number) DECEMBER 31, 2019 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to whic

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 16, 2019 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36558 (Comm

Amendment to Employment Agreement, dated December 9, 2019, to the Employment Agreement, dated October 16, 2017, by and between Townsquare Media, Inc. and Stuart Rosenstein

EXECUTION VERSION December 9, 2019 Stuart Rosenstein Address on file with the Company Re: Amendment to Employment Agreement Dear Stuart: This letter confirms our recent discussions regarding certain changes to your Employment Agreement, dated October 16, 2017 (the “Employment Agreement”), with Townsquare Media, Inc.

Amendment to Employment Agreement, dated December 9, 2019, to the Employment Agreement, dated October 25, 2017, by and between Townsquare Media, Inc. and Erik Hellum.

EXECUTION VERSION December 9, 2019 Erik Hellum Address on file with the Company Re: Amendment to Employment Agreement Dear Erik: This letter confirms our recent discussions regarding certain changes to your Employment Agreement, dated October 25, 2017 (the “Employment Agreement”), with Townsquare Media, Inc.

Amendment to Letter Agreement, dated December 9, 2019, to the Letter Agreement, dated October 16, 2017, and between Townsquare Media, Inc, and Steven Price

EXECUTION VERSION December 9, 2019 Steven Price Address on file with the Company Re: Amendment to Letter Agreement Dear Steven: This letter confirms our recent discussions regarding certain changes to your Letter Agreement, dated October 16, 2017 (the “Letter Agreement”), with Townsquare Media, Inc.

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 13, 2019 (December 9, 2019) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organizati

Second Amendment, dated December 9, 2019, to the Employment Agreement, dated October 16, 2017, as amended on April 24, 2019, by and between Townsquare Media, Inc. and Bill Wilson

EXECUTION VERSION December 9, 2019 Bill Wilson Address on file with the Company Re: Second Amendment to Employment Agreement Dear Bill: This letter confirms our recent discussions regarding certain changes to your Employment Agreement, as amended April 27, 2018 (the “Employment Agreement”), with Townsquare Media, Inc.

TOWNSQUARE ANNOUNCES STRONG THIRD QUARTER NET REVENUE GROWTH OF 8% AND ADJUSTED EBITDA GROWTH OF 13% (EX-POLITICAL) Raising 2019 Adjusted EBITDA Guidance Digital Revenue 35% of Total Net Revenue 4.7x Net Leverage1

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES STRONG THIRD QUARTER NET REVENUE GROWTH OF 8% (EX-POLITICAL) AND ADJUSTED EBITDA GROWTH OF 13% (EX-POLITICAL) Raising 2019 Adjusted EBITDA Guidance Digital Revenue 35% of Total Net Revenue 4.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 September 30, 2019 Date of Report (date of earliest event reported) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organi

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2019 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsq

TOWNSQUARE ANNOUNCES STRONG THIRD QUARTER NET REVENUE GROWTH OF 8% AND ADJUSTED EBITDA GROWTH OF 13% (EX-POLITICAL) Raising 2019 Adjusted EBITDA Guidance Digital Revenue 35% of Total Net Revenue 4.7x Net Leverage1

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES STRONG THIRD QUARTER NET REVENUE GROWTH OF 8% (EX-POLITICAL) AND ADJUSTED EBITDA GROWTH OF 13% (EX-POLITICAL) Raising 2019 Adjusted EBITDA Guidance Digital Revenue 35% of Total Net Revenue 4.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 September 30, 2019 Date of Report (date of earliest event reported) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organiza

TSQ / Townsquare Media, Inc. NT 10-Q - - NT 10-Q

SEC FILE NUMBER 001-36558 CUSIP NUMBER 892231 101 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2019 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 30, 2019 Date of Report (date of earliest event reported) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware 001-36558 27-1996555 (State or other jurisdiction of incorporation or organization)

TOWNSQUARE ANNOUNCES STRONG SECOND QUARTER NET REVENUE GROWTH OF 7% AND ADJUSTED EBITDA GROWTH OF 19% Raising 2019 Adjusted EBITDA Guidance Digital Revenue Over 33% of Total Net Revenue

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES STRONG SECOND QUARTER NET REVENUE GROWTH OF 7% AND ADJUSTED EBITDA GROWTH OF 19% Raising 2019 Adjusted EBITDA Guidance Digital Revenue Over 33% of Total Net Revenue Purchase, NY - August 6, 2019 - Townsquare Media, Inc.

Financial Statements and Exhibits, Changes in Registrant's Certifying Accountant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 19, 2019 (June 13, 2019) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 333

Letter to Securities and Exchange Commission from RSM US LLP, dated June 19, 2019

Exhibit 16.1 June 19, 2019 Securities and Exchange Commission Washington, D.C. 20549 Commissioners: We have read Townsquare Media, Inc.’s statements included under Item 4.01 of its Form 8-K, which we understand will be filed on June 19, 2019 and we agree with such statements concerning our firm. /s/ RSM US LLP

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 3, 2019 (May 29, 2019) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 333-1

TSQ / Townsquare Media, Inc. PX14A6G PX14A6G

Name of Registrant: Townsquare Media, Inc. Name of persons relying on exemption: California Public Employees Retirement System (CalPERS) Address of persons relying on exemption: 400 Q Street, Sacramento, CA 95811 Written materials are submitted pursuant to Rule 14a-6(g)(1) promulgated under the Securities Exchange Act of 1934. Submission is not required of this filer under the terms of the Rule, b

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [X] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2019 OR [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media,

TOWNSQUARE ANNOUNCES STRONG FIRST QUARTER NET REVENUE GROWTH OF 6.5% AND ADJUSTED EBITDA INCREASE 8.3% Digital Revenue Over 33% of Total Net Revenue for the First Time Ever

IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES STRONG FIRST QUARTER NET REVENUE GROWTH OF 6.

Amendment No. 4, dated April 30, 2019, to the Credit Agreement, dated as of April 1, 2015 (as amended by the Incremental Amendment Agreement No. 1 dated as of September 1, 2015, Amendment No. 2 dated as of February 8, 2017 and Amendment No. 3 dated as of October 20, 2017), among Townsquare Media, Inc., each lender from time to time party thereto, Royal Bank of Canada, as administrative agent and collateral agent.

AMENDMENT NO. 4 AMENDMENT NO. 4, dated as of April 30, 2019 (this “Amendment”), to the Credit Agreement, dated as of April 1, 2015 (as amended by the Incremental Amendment Agreement No. 1 dated as of September 1, 2015, Amendment No. 2 dated as of February 8, 2017, Amendment No. 3 dated as of October 20, 2017 and as further amended, supplemented, amended and restated or otherwise modified from time

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 31, 2019 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36558 (Commiss

Entry into a Material Definitive Agreement

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 3, 2019 (April 30, 2019) Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-

TSQ / Townsquare Media, Inc. DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Definitive Proxy State

TSQ / Townsquare Media, Inc. DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) x Definitive Proxy State

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 31, 2018 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36558 (Comm

TOWNSQUARE REPORTS STRONG FOURTH QUARTER: NET REVENUE RISES 12% AND ADJUSTED EBITDA INCREASES 9% 2018 Digital Revenue over $120 Million and Nearly 30% of Total Net Revenue

IMMEDIATE RELEASE TOWNSQUARE REPORTS STRONG FOURTH QUARTER: NET REVENUE RISES 12% AND ADJUSTED EBITDA INCREASES 9% 2018 Digital Revenue over $120 Million and Nearly 30% of Total Net Revenue Greenwich, CT - March 12, 2019 - Townsquare Media, Inc.

List of Subsidiaries of Townsquare Media, Inc.

Subsidiaries of Townsquare Media, Inc. Exact Name of Subsidiaries of Registrant Jurisdiction of Incorporation or Organization Townsquare Live Events International, LLC Delaware Townsquare Next, LLC Delaware Townsquare Live Productions, LLC Delaware Townsquare Interactive, LLC Delaware Townsquare MMN, LLC Delaware Townsquare Commerce, LLC Delaware Townsquare Finance, LLC Delaware Townsquare Managem

Employment Agreement, between Townsquare Media, Inc. and Erik Hellum, dated October 25, 2017.

EXECUTION COPY EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (the “Agreement”) is entered into October 25, 2017 (the “Effective Date”) between Townsquare Media, Inc.

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K [X] ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2018 OR [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media, Inc.

Separation Agreement dated as of December 31, 2018, by and between Townsquare Media, Inc. and Dhruv Prasad.

Execution Version SEPARATION AGREEMENT This Separation Agreement (the “Agreement”) is made as of the December 31, 2018 (the “Effective Date”) by and between Dhruv Prasad (the “Executive”) and Townsquare Media, Inc.

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 31, 2018 Townsquare Media, Inc.

TOWNSQUARE ANNOUNCES DEPARTURE OF CO-CHIEF EXECUTIVE OFFICER DHRUV PRASAD; BILL WILSON TO SERVE AS SOLE CHIEF EXECUTIVE OFFICER

EX-99.1 3 ex991tsqmanagementpressrel.htm EXHIBIT 99.1 IMMEDIATE RELEASE TOWNSQUARE ANNOUNCES DEPARTURE OF CO-CHIEF EXECUTIVE OFFICER DHRUV PRASAD; BILL WILSON TO SERVE AS SOLE CHIEF EXECUTIVE OFFICER Greenwich, CT – January 2, 2019 - Townsquare Media, Inc. (NYSE: TSQ) (“Townsquare” or the “Company”) announced today the departure of its Co-Founder and Co-Chief Executive Officer, Dhruv Prasad, who h

TOWNSQUARE REPORTS THIRD QUARTER 2018 RESULTS

IMMEDIATE RELEASE TOWNSQUARE REPORTS THIRD QUARTER 2018 RESULTS Greenwich, CT - November 6, 2018 - Townsquare Media, Inc.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 6, 2018 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36558 (Commi

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [X] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2018 OR [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Me

Form of Restricted Stock Award Agreement

RESTRICTED STOCK AWARD AGREEMENT PURSUANT TO THE TOWNSQUARE MEDIA, INC. 2014 OMNIBUS INCENTIVE PLAN * * * * * [GRANTEE] [DATE] * * * * * THIS RESTRICTED STOCK AWARD AGREEMENT (this “Agreement”), dated as of the date specified above (the “Grant Date”), is entered into by and between Townsquare Media, Inc., a Delaware corporation (the “Company”), and [GRANTEE] (the “Participant”), pursuant to the To

TSQ / Townsquare Media, Inc. SC TO-I/A

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO (Amendment No. 5) (Rule 13e-4) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 TOWNSQUARE MEDIA, INC. (Name Of Subject Company (Issuer) and Filing Person (Offeror)) OPTIONS TO PURCHASE SHARES OF COMMON STOCK, PAR VALUE $0.01 PER SHARE (Title of Class of Securities) 892231101 (CUSI

FORM OF COMMUNICATION REGARDING THE RESULTS OF THE OPTION EXCHANGE OFFER

Exhibit (a)(1)(K) FORM OF COMMUNICATION REGARDING THE RESULTS OF THE OPTION EXCHANGE OFFER TO: Eligible Participants FROM: Chris Kitchen, Executive Vice President and General Counsel SUBJECT: Results of the Option Exchange Offer Program The option exchange offer expired at 11:59 p.

TSQ / Townsquare Media, Inc. SC TO-I/A

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO (Amendment No. 4) (Rule 13e-4) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 TOWNSQUARE MEDIA, INC. (Name Of Subject Company (Issuer) and Filing Person (Offeror)) OPTIONS TO PURCHASE SHARES OF COMMON STOCK, PAR VALUE $0.01 PER SHARE (Title of Class of Securities) 892231101 (CUSI

Screen Shot of Intranet Page Displaying Final Exchange Ratios and Replacement Option Exercise Price Townsquare Media, Inc. Option Exchange Offer Final Exchange Ratios and Replacement Option Exercise Price August 16, 2018

Exhibit (a)(1)(V) Screen Shot of Intranet Page Displaying Final Exchange Ratios and Replacement Option Exercise Price Townsquare Media, Inc.

EMAIL REGARDING FINAL EXCHANGE RATIOS AND REPLACEMENT OPTION EXERCISE PRICE

Exhibit (a)(1)(T) EMAIL REGARDING FINAL EXCHANGE RATIOS AND REPLACEMENT OPTION EXERCISE PRICE FROM: Chris Kitchen, Executive Vice President and General Counsel SUBJECT: Option Exchange Offer Program Closes Today DATE: August 16, 2018 Today is the last day to elect to exchange your eligible stock options as part of the Company’s Offer to Exchange Eligible Options for Replacement Options (referred to as the “Offer to Exchange”).

TSQ / Townsquare Media, Inc. SC TO-I/A

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO (Amendment No. 3) (Rule 13e-4) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 TOWNSQUARE MEDIA, INC. (Name Of Subject Company (Issuer) and Filing Person (Offeror)) OPTIONS TO PURCHASE SHARES OF COMMON STOCK, PAR VALUE $0.01 PER SHARE (Title of Class of Securities) 892231101 (CUSI

FORM OF EMAIL REGARDING UPDATED HYPOTHETICAL EXCHANGE RATIOS

Exhibit (a)(1)(R) FORM OF EMAIL REGARDING UPDATED HYPOTHETICAL EXCHANGE RATIOS FROM: Chris Kitchen, Executive Vice President and General Counsel SUBJECT: Option Exchange Offer Program Deadline Approaching DATE: August 13, 2018 This email is to remind you that August 16, 2018 at 11:59 p.

TOWNSQUARE MEDIA, INC. July 18, 2018, as amended on July 31, 2018 and August 13, 2018 OFFER TO EXCHANGE ELIGIBLE OPTIONS FOR REPLACEMENT OPTIONS This offer to exchange and your associated withdrawal rights will expire at 11:59 p.m., Eastern Time, on

Exhibit (a)(1)(A) TOWNSQUARE MEDIA, INC. July 18, 2018, as amended on July 31, 2018 and August 13, 2018 OFFER TO EXCHANGE ELIGIBLE OPTIONS FOR REPLACEMENT OPTIONS This offer to exchange and your associated withdrawal rights will expire at 11:59 p.m., Eastern Time, on August 16, 2018 (the “Expiration Date”), unless extended. Townsquare Media, Inc., a Delaware corporation, which is sometimes referre

TSQ / Townsquare Media, Inc. SC TO-I/A

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO (Amendment No. 2) (Rule 13e-4) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 TOWNSQUARE MEDIA, INC. (Name Of Subject Company (Issuer) and Filing Person (Offeror)) OPTIONS TO PURCHASE SHARES OF COMMON STOCK, PAR VALUE $0.01 PER SHARE (Title of Class of Securities) 892231101 (CUSI

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 8, 2018 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36558 (Commi

TOWNSQUARE REPORTS SECOND QUARTER 2018 RESULTS

IMMEDIATE RELEASE TOWNSQUARE REPORTS SECOND QUARTER 2018 RESULTS Greenwich, CT - August 8, 2018 - Townsquare Media, Inc.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 8, 2018 Townsquare Media, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-36558 (Commiss

TOWNSQUARE REPORTS SECOND QUARTER 2018 RESULTS

IMMEDIATE RELEASE TOWNSQUARE REPORTS SECOND QUARTER 2018 RESULTS Greenwich, CT - August 8, 2018 - Townsquare Media, Inc.

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [X] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2018 OR [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36558 Townsquare Media,

FORM OF REMINDERS OF EXPIRATION OF OPTION EXCHANGE OFFER

Exhibit (a)(1)(H) FORM OF REMINDERS OF EXPIRATION OF OPTION EXCHANGE OFFER FROM: Chris Kitchen, Executive Vice President and General Counsel SUBJECT: Option Exchange Offer Program Deadline Approaching DATE: August [•], 2018 This email is to remind you that August [16], 2018 at 11:59 p.

Screen Shot of Intranet Page Displaying Updated Hypothetical Exchange Ratios Townsquare Media, Inc. Option Exchange Offer Hypothetical Exchange Ratios August [•], 2018

Exhibit (a)(1)(S) Screen Shot of Intranet Page Displaying Updated Hypothetical Exchange Ratios Townsquare Media, Inc.

FORM OF EMAIL REGARDING UPDATED HYPOTHETICAL EXCHANGE RATIOS

Exhibit (a)(1)(R) FORM OF EMAIL REGARDING UPDATED HYPOTHETICAL EXCHANGE RATIOS FROM: Chris Kitchen, Executive Vice President and General Counsel SUBJECT: Option Exchange Offer Program Deadline Approaching DATE: August [13], 2018 This email is to remind you that August [16], 2018 at 11:59 p.

TSQ / Townsquare Media, Inc. SC TO-I

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE TO (Amendment No. 1) (Rule 13e-4) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 TOWNSQUARE MEDIA, INC. (Name Of Subject Company (Issuer) and Filing Person (Offeror)) OPTIONS TO PURCHASE SHARES OF COMMON STOCK, PAR VALUE $0.01 PER SHARE (Title of Class of Securities) 892231101 (CUSI

FORM OF FINAL REMINDER OF EXPIRATION OF EXCHANGE OFFER

Exhibit (a)(1)(I) FORM OF FINAL REMINDER OF EXPIRATION OF EXCHANGE OFFER FROM: Chris Kitchen, Executive Vice President, and General Counsel SUBJECT: Option Exchange Offer Program Deadline Tomorrow DATE: August [15], 2018 This email is to remind you that tomorrow, August [16], 2018 at 11:59 p.

TOWNSQUARE MEDIA, INC. July 18, 2018, as amended on July 31, 2018 OFFER TO EXCHANGE ELIGIBLE OPTIONS FOR REPLACEMENT OPTIONS This offer to exchange and your associated withdrawal rights will expire at 11:59 p.m., Eastern Time, on August 16, 2018 (the

Exhibit (a)(1)(A) TOWNSQUARE MEDIA, INC. July 18, 2018, as amended on July 31, 2018 OFFER TO EXCHANGE ELIGIBLE OPTIONS FOR REPLACEMENT OPTIONS This offer to exchange and your associated withdrawal rights will expire at 11:59 p.m., Eastern Time, on August 16, 2018 (the “Expiration Date”), unless extended. Townsquare Media, Inc., a Delaware corporation, which is sometimes referred to herein as the “

E-mail Regarding Amended Offer to Exchange and Additional Exchange Ratio Examples

Exhibit (a)(1)(Q) E-mail Regarding Amended Offer to Exchange and Additional Exchange Ratio Examples FROM: Chris Kitchen, Executive Vice President, and General Counsel SUBJECT: Townsquare Offer to Exchange Eligible Options for Replacement Options DATE: July 31, 2018 On July 31, 2018, Townsquare Media, Inc.

EMAIL REGARDING FINAL EXCHANGE RATIOS AND REPLACEMENT OPTION EXERCISE PRICE

Exhibit (a)(1)(T) EMAIL REGARDING FINAL EXCHANGE RATIOS AND REPLACEMENT OPTION EXERCISE PRICE FROM: Chris Kitchen, Executive Vice President and General Counsel SUBJECT: Option Exchange Offer Program Closes Today DATE: August [16], 2018 Today is the last day to elect to exchange your eligible stock options as part of the Company’s Offer to Exchange Eligible Options for Replacement Options (referred to as the “Offer to Exchange”).

TSQ / Townsquare Media, Inc. CORRESP

TELEPHONE: 1-212-558-4000 FACSIMILE: 1-212-558-3588 WWW.SULLCROM.COM 125 Broad Street New York, New York 10004-2498 LOS ANGELES • PALO ALTO • WASHINGTON, D.C. BRUSSELS • FRANKFURT • LONDON • PARIS BEIJING • HONG KONG • TOKYO MELBOURNE • SYDNEY July 31, 2018 Via EDGAR Ms. Tiffany Posil Special Counsel Division of Corporation Finance Office of Mergers & Acquisitions United States Securities and Exch

NONQUALIFIED STOCK OPTION AWARD AGREEMENT PURSUANT TO THE TOWNSQUARE MEDIA, INC. 2014 OMNIBUS INCENTIVE PLAN * * * * *

Exhibit (a)(1)(M) NONQUALIFIED STOCK OPTION AWARD AGREEMENT PURSUANT TO THE TOWNSQUARE MEDIA, INC.