SCHEDULE 13D | High Roller Technologies, Inc.

SCHEDULE 13D

CUSIP Number(s):

42981K100

Name of reporting person

Cascadia Holdings Ltd

Check the appropriate box if a member of a Group (See Instructions)

(a)

(b)

SEC use only

Source of funds (See Instructions)

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

Checkbox not checked

Citizenship or place of organization

MALTA

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 2,644,423.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 2,644,423.00

Aggregate amount beneficially owned by each reporting person

2,644,423.00

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Percent of class represented by amount in Row (11)

24 %

Type of Reporting Person (See Instructions)

Comment for Type of Reporting Person:

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.

SCHEDULE 13D

CUSIP Number(s):

42981K100

Name of reporting person

Brandon Eachus

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(a)

(b)

SEC use only

Source of funds (See Instructions)

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

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Citizenship or place of organization

UNITED STATES

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 104,968.00
8	Shared Voting Power 2,644,423.00
9	Sole Dispositive Power 104,968.00
10	Shared Dispositive Power 2,644,423.00

Aggregate amount beneficially owned by each reporting person

2,749,391.00

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Percent of class represented by amount in Row (11)

24.9 %

Type of Reporting Person (See Instructions)

Comment for Type of Reporting Person:

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.

SCHEDULE 13D

CUSIP Number(s):

42981K100

Name of reporting person

Michael Cribari

Check the appropriate box if a member of a Group (See Instructions)

(a)

(b)

SEC use only

Source of funds (See Instructions)

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

Checkbox not checked

Citizenship or place of organization

UNITED STATES

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 61,052.00
8	Shared Voting Power 2,644,423.00
9	Sole Dispositive Power 61,052.00
10	Shared Dispositive Power 2,644,423.00

Aggregate amount beneficially owned by each reporting person

2,705,475.00

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

Checkbox not checked

Percent of class represented by amount in Row (11)

24.5 %

Type of Reporting Person (See Instructions)

Comment for Type of Reporting Person:

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.

SCHEDULE 13D

Item 1.

Security and Issuer

(a)

Title of Class of Securities:

Common Stock, $0.001 par value per share

(b)

Name of Issuer:

High Roller Technologies, Inc.

(c)

Address of Issuer's Principal Executive Offices:

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

Item 1 Comment:

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.

Item 5.

Interest in Securities of the Issuer

(a)

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.

(b)

The information contained on the cover pages to this Amendment is incorporated by reference herein.

(c)

The Reporting Persons have not engaged in any transaction during the past 60 days involving the Common Stock of the Issuer.

(d)

Not applicable.

(e)

Not applicable.

Item 7.

Material to be Filed as Exhibits.

None

SIGNATURE

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

Cascadia Holdings Ltd

Signature:	/s/ Brandon Eachus
Name/Title:	Brandon Eachus, Director
Date:	05/29/2026

Brandon Eachus

Signature:	/s/ Brandon Eachus
Name/Title:	Brandon Eachus
Date:	05/29/2026

Michael Cribari

Signature:	/s/ Michael Cribari
Name/Title:	Michael Cribari
Date:	05/29/2026