| 1. Round | 09/03/2025 | Lexington SC | - | Hartford Athletic | 2:0 | ||||
| 3. Round | 22/03/2025 | Pittsburgh Riverhounds | - | Hartford Athletic | 1:0 | ||||
| 4. Round | 29/03/2025 | Hartford Athletic | - | El Paso Locomotive | 1:2 | ||||
| 5. Round | 05/04/2025 | Loudoun United | - | Hartford Athletic | 2:0 | ||||
| 7. Round | 19/04/2025 | Hartford Athletic | - | Birmingham Legion | 1:0 | ||||
| 8. Round | 03/05/2025 | Charleston Battery | - | Hartford Athletic | 4:2 |  |
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| 9. Round | 11/05/2025 | Hartford Athletic | - | Detroit City FC | 0:0 | ||||
| 10. Round | 18/05/2025 | Hartford Athletic | - | Louisville City FC | 1:1 | ||||
| 11. Round | 29/05/2025 | Indy Eleven | - | Hartford Athletic | 4:4 | |
Jamaica