Company: GAME
Filing Date: 2025-07-18
Form Type: 424B5
Source: 0001641172-25-020129
Chunk: 0

Company: GameSquare Holdings, Inc.
Filing Date: 2025-07-18
Form: 424B5
Chunk 0
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Filed Pursuant to Rule 424(b)(5)

File No. 333-285543

PRELIMINARY PROSPECTUS SUPPLEMENT
(to Prospectus dated May 9, 2025)

<div align='center'>GAMESQUARE HOLDINGS, INC.

46,666,667shares of Common Stock</div>

We are offering 46,666,667
shares of our Common Stock, par value $0.0001 per share (the “Common Stock”), pursuant to this Prospectus Supplement
and accompanying Prospectus.

Our Common Stock is listed on The Nasdaq Capital Market (“NASDAQ”)
under the symbol “GAME.” On July 15, 2025, the last reported sale price of our Common Stock on NASDAQ was $1.66.

We are an “emerging growth company” as defined in Section 2(a) of the Securities Act of 1933 (the “ Securities Act”) and a “smaller reporting company” as defined under Rule 405 of the Securities Act, and as such, we have elected to comply with certain reduced public company reporting requirements. See “Summary- Implications of Being an Emerging Growth Company and a Smaller Reporting Company.”

Investing in our securities involves a high degree of risk. See“ Risk Factors” section beginning on page S-12 of this prospectus supplement and any other risk factors contained in any applicable prospectus supplement and in the documents incorporated by reference herein and therein.

NEITHER THE UNITED STATES SECURITIES AND EXCHANGE COMMISSION (THE “SEC”) NOR ANY STATE SECURITIES COMMISSION OR REGULATOR HAS APPROVED OR DISAPPROVED THESE SECURITIES, NOR PASSED UPON THE ADEQUACY OR ACCURACY OF THE PROSPECTUS OR THIS PROSPECTUS SUPPLEMENT. ANY REPRESENTATION TO THE CONTRARY IS A CRIMINAL OFFENCE.

|                                           |     | Per Share |       |     | Total                         
 Without Over-Allotment Option |               |     | With Over Allotment Option |               |
|:------------------------------------------|:----|:----------|------:|:----|:------------------------------|--------------:|:----|:---------------------------|--------------:|
| Public offering price                     |     | $         |  1.50 |     | $                             | 70,000,000.50 |     | $                          | 80,500,000.50 |
| Underwriting discounts and commissions(1) |     | $         |