| 5. Round | 05/08/2021 | Hartford Athletic | - | Miami FC | 1:1 | ||||
| 5. Round | 08/08/2021 | Colorado Springs Switchbacks | - | Hartford Athletic | 4:2 | ||||
| 5. Round | 29/08/2021 | Hartford Athletic | - | Pittsburgh Riverhounds | 2:3 | ||||
| 6. Round | 05/09/2021 | New York RB II | - | Hartford Athletic | 2:0 | ||||
| 7. Round | 01/10/2021 | Hartford Athletic | - | Charlotte Independence | 1:2 | ||||
| 7. Round | 10/10/2021 | Charleston Battery | - | Hartford Athletic | 4:3 |  |
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| 7. Round | 23/10/2021 | Hartford Athletic | - | Charlotte Independence | 1:2 |
USA