X0202 SCHEDULE 13D/A 0002009695 XXXXXXXX LIVE 2 Common Stock, $0.001 par value per share 04/28/2026 false 0001947210 42981K100 High Roller Technologies, Inc.

400 South 4th Street, Suite 500-#390 Las Vegas NV 89101

Brandon Eachus (702) 509-5244 c/o High Roller Technologies, Inc. 400 South 4th Street, Suite 500-#390 Las Vegas NV 89101 0002009695 N Cascadia Holdings Ltd b PF N O1 0.00 2644423.00 0.00 2644423.00 2644423.00 N 24 OO Securities disclosed herein consist of (i) 1,800,748 shares of the Issuer's common stock, par value $0.001 per share, held directly by Cascadia Holdings Limited ("Cascadia") and (ii) 804,503 shares of common stock and warrants to purchase 39,172 shares of common stock, beneficially held by Spike Up Media A.B. and Spike Up Media LLC, indirect wholly owned subsidiaries of Cascadia. Beneficial ownership is based on 11,008,699 shares of common stock outstanding. Y Brandon Eachus b PF N X1 104968.00 2644423.00 104968.00 2644423.00 2749391.00 N 24.9 IN Securities disclosed herein consist of (i) 89,968 shares of common stock and fully vested options to purchase additional 15,000 shares of common stock of the Issuer held directly by Mr. Eachus, (ii) 1,800,748 shares of common stock held directly by Cascadia Holdings Limited ("Cascadia") and (iii) 804,503 shares of common stock and warrants to purchase 39,172 shares of common stock, beneficially held by Spike Up Media A.B. and Spike Up Media LLC, which are indirect wholly owned subsidiaries of Cascadia. Beneficial ownership is based on 11,023,699 shares of common stock outstanding. Excludes derivative securities not exercisable within 60 days from the date of the filing of this Amendment No.2 to Schedule 13D. Y Michael Cribari b PF N X1 61052.00 2644423.00 61052.00 2644423.00 2705475.00 N 24.5 IN Securities disclosed herein consist of (i) 46,052 shares of common stock and fully vested options to purchase additional 15,000 shares of common stock of the Issuer held directly by Mr. Cribari, (ii) 1,800,748 shares of common stock held directly by Cascadia Holdings Limited ("Cascadia") and (iii) 804,503 shares of common stock and warrants to purchase 39,172 shares of common stock, beneficially held by Spike Up Media A.B. and Spike Up Media LLC, indirect wholly owned subsidiaries of Cascadia. Beneficial ownership is based on 11,023,699 shares of common stock outstanding. Excludes derivative securities not exercisable within 60 days from the date of the filing of this Amendment No.2 to Schedule 13D. Common Stock, $0.001 par value per share High Roller Technologies, Inc. 400 South 4th Street, Suite 500-#390 Las Vegas NV 89101 This Amendment No. 2 amends and supplements the Schedule 13D filed with the U.S. Securities and Exchange Commission (the "SEC") on November 5, 2024, as amended by Amendment No. 2 filed with the SEC on November 5, 2024, relating to the common stock of High Roller Technologies, Inc., a Delaware corporation (the "Issuer"). Except as set forth herein, the Schedule 13D is unmodified and remains in full force and effect. Each capitalized term used but not defined herein has the meaning ascribed to such term in the Schedule 13D. 1. As of April 28, 2026, pursuant to share redemption agreement between Cascadia and Jeff Smith, Cascadia distributed 787,648 shares of common stock of the Issuer to Mr. Smith pro rata to his interest in Cascadia for no additional consideration (the "Distribution"). 2. Following the Distribution, Mr. Smith ceased to be a beneficial owner of the shares of common stock of the Issuer held by Cascadia and no longer has shared voting or shared dispositive power over shares of common stock of the Issuer held by Cascadia. Mr. Smith may be deemed to have a limited pecuniary interest in the Issuer shares held indirectly by Ellmount. The information contained on the cover pages to this Amendment is incorporated by reference herein. The Reporting Persons have not engaged in any transaction during the past 60 days involving the Common Stock of the Issuer. Not applicable. Not applicable. None Cascadia Holdings Ltd /s/ Brandon Eachus 05/29/2026 Brandon Eachus /s/ Brandon Eachus 05/29/2026 Michael Cribari /s/ Michael Cribari 05/29/2026