| 2. Round | 16/03/2025 | Monterey Bay FC | - | Oakland Roots | 3:2 | ||||
| 3. Round | 23/03/2025 | Oakland Roots | - | San Antonio FC | 1:2 | ||||
| 4. Round | 30/03/2025 | Oakland Roots | - | Las Vegas Lights FC | 0:0 | ||||
| 5. Round | 05/04/2025 | Oakland Roots | - | Rhode Island FC | 0:3 | ||||
| 6. Round | 13/04/2025 | FC Tulsa | - | Oakland Roots | 1:2 |  |
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| 7. Round | 19/04/2025 | Oakland Roots | - | Orange County SC | 2:0 | |
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| 8. Round | 05/05/2025 | Oakland Roots | - | Sacramento Republic | 0:1 | ||||
| 9. Round | 11/05/2025 | San Antonio FC | - | Oakland Roots | 1:2 | ||||
| 10. Round | 17/05/2025 | North Carolina FC | - | Oakland Roots | 4:2 | |
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| 11. Round | 25/05/2025 | Oakland Roots | - | New Mexico United | 0:3 | |
Trinidad & Tobago