| 2. Round | 01/05/2021 | New York RB II | - | Hartford Athletic | 2:3 | ||||
| 2. Round | 09/05/2021 | Miami FC | - | Hartford Athletic | 0:1 | ||||
| 2. Round | 16/05/2021 | Hartford Athletic | - | Pittsburgh Riverhounds | 1:1 |  |
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| 6. Round | 05/09/2021 | New York RB II | - | Hartford Athletic | 2:0 | ||||
| 6. Round | 12/09/2021 | Charlotte Independence | - | Hartford Athletic | 2:0 | ||||
| 6. Round | 16/09/2021 | Hartford Athletic | - | Real Monarchs SLC | 2:0 | ||||
| 7. Round | 01/10/2021 | Hartford Athletic | - | Charlotte Independence | 1:2 | ||||
| 7. Round | 10/10/2021 | Charleston Battery | - | Hartford Athletic | 4:3 | ||||
| 7. Round | 14/10/2021 | Loudoun United | - | Hartford Athletic | 2:3 | ||||
| 7. Round | 17/10/2021 | Hartford Athletic | - | Loudoun United | 1:0 | ||||
| 7. Round | 23/10/2021 | Hartford Athletic | - | Charlotte Independence | 1:2 |  |
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| 7. Round | 27/10/2021 | Hartford Athletic | - | Charleston Battery | 2:0 | ||||
| 7. Round | 31/10/2021 | Pittsburgh Riverhounds | - | Hartford Athletic | 0:0 |
USA