ROLR · High Roller Technologies, Inc. · Insider Trading

The price reported in Column 4 represents a weighted average sales price. These shares were sold in multiple transactions at prices ranging from $6.08 to $6.345, inclusive.

Represents shares sold pursuant to a Rule 10b5-1 Plan adopted by the Reporting Person on May 14, 2026, to satisfy tax withholding obligations in connection with the vesting of restricted stock units ("RSU").

Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of the Issuer's common stock, subject to the applicable vesting schedule and conditions of each RSU.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The number of shares subject to the options shall vest and become exercisable on December 31, 2026. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The number of shares subject to the options shall vest and become exercisable on December 31, 2026. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The number of shares subject to the options shall vest and become exercisable on December 31, 2026. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The number of shares subject to the options shall vest and become exercisable on December 31, 2026. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The number of shares subject to the options shall vest and become exercisable on December 31, 2026. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The number of shares subject to the options shall vest and become exercisable on December 31, 2026. The options have a maximum term of ten (10) years from the date of grant.

Represents the number of shares of Common Stock withheld by the Issuer to satisfy its tax withholding and remittance obligations in connection with the net settlement of restricted stock units ("RSUs") and does not represent a sale by the Reporting Person.

Certain of these securities are RSUs. Each RSU represents a contingent right to receive one share of the Issuer's common stock, subject to the applicable vesting schedule and conditions of each RSU.

Cascadia Holdings Ltd. ("Cascadia") distributed 787,648 shares of common stock of High Roller Technologies, Inc. ("Company") to one of its shareholders, pro rata to his interest for no additional consideration, pursuant to share redemption agreement between that shareholder and Cascadia.

The reported transaction involved the Reporting Person's receipt of 100,000 restricted stock units ("RSUs"). The RSUs were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. Each RSU represents a contingent right to receive one share of common stock upon vesting. Of the total RSUs reported, 40,000 RSUs shall vest in equal quarterly installments over a period of three years, and the remaining 60,000 RSUs are subject to vesting upon the achievement of certain performance conditions, as determined and certified by the board of directors of the Issuer, subject to the Reporting Person's continued service.

The total reported in Column 5 includes (i) the 100,000 newly awarded RSUs, (ii) 50,000 RSUs of which 12,500 have vested, and (iii) 14,550 shares of common stock.

The reported transaction involved the Reporting Person's receipt of 120,500 restricted stock units ("RSUs"). The RSUs were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. Each RSU represents a contingent right to receive one share of common stock upon vesting. Of the total RSUs reported, 70,000 RSUs shall vest in equal quarterly installments over a period of three years, and the remaining 50,500 RSUs are subject to vesting upon the achievement of certain performance conditions, as determined and certified by the board of directors of the Issuer, subject to the Reporting Person's continued service.

The total reported in Column 5 includes (i) the 120,500 newly awarded RSUs, (ii) 75,000 RSUs of which 0 have vested and (iii) 12,796 shares of common stock.

The reported transaction involved open market purchases of shares in accordance with Issuer's trading policies.

The total reported in Column 5 includes (i) 5,022 shares of common stock and (ii) 10,000 restricted stock units, of which none have vested.

The reported transaction involved the Reporting Person's receipt of 10,000 restricted stock units ("RSUs"). The RSUs were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The RSUs shall vest in equal quarterly installments over a period of three years commencing six months after the date of employment and subject to continued service with the Company. The total reported in Column 5 includes the 10,000 newly awarded restricted stock units and 2,745 shares of common stock.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The options shall vest and become exercisable in equal quarterly installments over a period of three years commencing six months after the date of employment and subject to continued service with the Company. The options have a maximum term of ten (10) years from the date of grant.

Open market purchase of shares in accordance with Issuer's trading policies.

Open market purchases of shares in accordance with Issuer's trading policies.

The price reported in Column 4 represents a weighted average sales price. These Shares were sold in multiple transactions at prices ranging from $1.89 to $1.94, inclusive.

Open market purchases of shares in accordance with Issuer's trading policies.

The price reported in Column 4 represents a weighted average sales price. These Shares were sold in multiple transactions at prices ranging from $1.76 to $1.81, inclusive.

Open market purchases of shares in accordance with Issuer's trading policies.

Open market purchases of shares in accordance with Issuer's trading policies.

Open market purchases of shares in accordance with Issuer's trading policies.

Open market purchases of shares in accordance with Issuer's trading policies.

The reported price in Column 4 is a weighted average purchase price. These shares were purchased in multiple transactions at prices ranging from $2.375 to $2.60 per share. The Reporting Person undertakes to provide to the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the range set forth in this footnote.

Open market purchase of shares in accordance with Issuer's trading policies.

The reported price in Column 4 is a weighted average purchase price. These shares were purchased in multiple transactions at prices ranging from $2.345 to $2.44 per share. The Reporting Person undertakes to provide to the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the range set forth in this footnote.

Open market purchase of shares in accordance with Issuer's trading policies.

The reported price in Column 4 is a weighted average purchase price. These shares were purchased in multiple transactions at prices ranging from $2.35 to $2.58 per share. The Reporting Person undertakes to provide to the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the range set forth in this footnote.

The reported transaction involved the Reporting Person's receipt of 24,079 restricted shares of common stock pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan.

Open market purchase of shares in accordance with Issuer's trading policies.

The reported price in Column 4 is a weighted average purchase price. These shares were purchased in multiple transactions at prices ranging from $2.80 to $3.22 per share. The Reporting Person undertakes to provide to the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the range set forth in this footnote.

Open market purchase of shares in accordance with Issuer's trading policies.

The reported price in Column 4 is a weighted average purchase price. These shares were purchased in multiple transactions at prices ranging from $2.34 to $2.70 per share. The Reporting Person undertakes to provide to the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the range set forth in this footnote.

Open market purchase of shares in accordance with Issuer's trading policies.

The reported price in Column 4 is a weighted average purchase price. These shares were purchased in multiple transactions at prices ranging from $1.95 to $2.02 per share. The Reporting Person undertakes to provide to the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the range set forth in this footnote.

Open market purchases of shares in accordance with Issuer's trading policies.

Open market purchase of shares in accordance with Issuer's trading policies.

The reported price in Column 4 is a weighted average purchase price. These shares were purchased in multiple transactions at prices ranging from $2.33 to $2.43 per share. The Reporting Person undertakes to provide to the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the range set forth in this footnote.

Open market purchases of shares in accordance with Issuer's trading policies.

Open market purchases of shares in accordance with Issuer's trading policies.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The options shall vest and become exercisable in equal quarterly installments over a period of three years. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The options shall vest and become exercisable in equal quarterly installments over a period of three years. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The options shall vest and become exercisable in equal quarterly installments over a period of three years. The options have a maximum term of ten (10) years from the date of grant.

The reported transaction involved the Reporting Person's receipt of 50,000 restricted stock units ("RSUs"). The RSUs were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The RSUs shall vest in equal quarterly installments over a period of three years.

The reported transaction involved the Reporting Person's receipt of 75,000 restricted stock units ("RSUs"). The RSUs were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. 1/12th of the total number of shares subject to the RSUs shall vest on January 1, 2025, with the remainder vesting in 1/12th increments quarterly.

The reported transaction involved the Reporting Person's receipt of 50,000 restricted stock units ("RSUs"). The RSUs were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. 1/12th of the total number of shares subject to the RSUs shall vest on January 1, 2025, with the remainder vesting in 1/12th increments quarterly.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The number of shares subject to the options shall vest and become exercisable on October 31, 2025. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. 1/12th of the total number of shares subject to the options shall vest and become exercisable on January 1, 2025, with the remainder vesting in 1/12th increments quarterly. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The number of shares subject to the options shall vest and become exercisable on October 31, 2025. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The number of shares subject to the options shall vest and become exercisable on October 31, 2025. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. 1/12th of the total number of shares subject to the options shall vest and become exercisable on January 1, 2025, with the remainder vesting in 1/12th increments quarterly. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The number of shares subject to the options shall vest and become exercisable on October 31, 2025. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The number of shares subject to the options shall vest and become exercisable on October 31, 2025. The options have a maximum term of ten (10) years from the date of grant.

The options were granted pursuant to the High Roller Technologies, Inc. 2024 Equity Incentive Plan. The number of shares subject to the options shall vest and become exercisable on October 31, 2025. The options have a maximum term of ten (10) years from the date of grant.