GameSquare Holdings, Inc.

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

Check the appropriate box:

(Name of Registrant as Specified In Its Charter)

Name of Person(s) Filing Proxy Statement, if other than the Registrant

Payment of Filing Fee (Check the appropriate box):

6775 Cowboys Way, Ste. 1335

Frisco, Texas 75034

NOTICE OF SPECIAL MEETING OF STOCKHOLDERS

To Be Held at 12:00 p.m. Central Time on October 22, 2026

Dear GameSquare Holdings, Inc. Stockholder:

You are cordially invited to attend our special meeting of stockholders (the “Special Meeting”), which will be held on October 22, 2026 at 12:00 p.m. Central Time. The Special Meeting will be conducted virtually via live webcast. You will be able to vote and submit your questions during the meeting by visiting https://meetnow.global/MDS5HNF. Please have your notice or proxy card in hand when you visit the website. During the Special Meeting, stockholders will be asked to vote on the following proposals, as more fully described in the accompanying proxy statement:

1. To approve, for purposes of complying with Nasdaq Listing Rule 5635(a), the issuance of shares of our Common Stock, issuable pursuant to that certain Contribution Agreement, dated as of September 8, 2026 (the “Contribution Agreement”), by and among the Company, GameSquare IP Holdings, Inc., a Delaware corporation and wholly owned subsidiary of the Company, FanEngine Holdings Ltd., a private limited company organized under the laws of England and Wales (“FanEngine”), the Seller Securityholders party thereto (the “Seller Securityholders”), and Jesper Schertiger, solely in his capacity as representative of the Seller Securityholders, including shares issuable pursuant to earnout provisions thereunder, in an amount in excess of 20% of all of the Company’s Common Stock outstanding immediately prior to the closing of the transactions contemplated by the Contribution Agreement (the “Issuance Proposal”);

2. To approve the GameSquare Holdings, Inc. 2026 Stock Incentive Plan (the “Incentive Plan Proposal”);

3. To approve an adjournment of the Special Meeting, if necessary or appropriate, to solicit additional proxies; and

4. To transact such other business as may properly come before the Special Meeting or any adjournments or postponements thereof.

Our Board of Directors has fixed the close of business on September 21, 2026 as the record date for the Special Meeting. Only stockholders of record on September 21, 2026 are entitled to notice of and to vote at the Special Meeting. It is important that your shares are represented and voted at the Special Meeting. For specific voting instructions, please refer to the information provided in the proxy statement, together with your proxy card or the voting instructions you received with the proxy statement.

Your vote must be received by 12:00 p.m. Central Time, on October 20, 2026. For specific voting instructions, please refer to the information provided in the proxy statement, together with your proxy card or the voting instructions you received with the proxy statement. This proxy statement is being mailed to stockholders on or about October 2, 2026.

YOUR VOTE IS IMPORTANT. Whether or not you plan to attend the virtual Special Meeting, we request that you submit your vote via the Internet, telephone or mail.

Thank you for your continued support of GameSquare Holdings, Inc.

By Order of the Board of Directors,

/s/ Justin Kenna

Justin Kenna

Chief Executive Officer and Director

Frisco, Texas

October 2, 2026

TABLE OF CONTENTS

PROXY STATEMENT

FOR THE SPECIAL MEETING OF STOCKHOLDERS

To Be Held at 12:00 p.m. Central Time on October 22, 2026