| 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 | ||||
| 3. Round | 06/06/2021 | Hartford Athletic | - | New York RB II | 7:0 | ||||
| 3. Round | 14/06/2021 | Charlotte Independence | - | Hartford Athletic | 3:2 | ||||
| 4. Round | 25/07/2021 | Hartford Athletic | - | Miami FC | 2:0 | ||||
| 4. Round | 01/08/2021 | Pittsburgh Riverhounds | - | Hartford Athletic | 3:1 | ||||
| 5. Round | 05/08/2021 | Hartford Athletic | - | Miami FC | 1:1 |  |
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| 5. Round | 08/08/2021 | Colorado Springs Switchbacks | - | Hartford Athletic | 4:2 | ||||
| 5. Round | 14/08/2021 | Tampa Bay Rowdies | - | Hartford Athletic | 1:0 | ||||
| 6. Round | 05/09/2021 | New York RB II | - | Hartford Athletic | 2:0 | ||||
| 7. Round | 10/10/2021 | Charleston Battery | - | Hartford Athletic | 4:3 | ||||
| 7. Round | 14/10/2021 | Loudoun United | - | Hartford Athletic | 2:3 |
USA