| 2. Round | 03/05/2021 | Miami FC | - | Loudoun United | 2:1 | ||||
| 3. Round | 09/06/2021 | Loudoun United | - | Charleston Battery | 0:1 | ||||
| 3. Round | 20/06/2021 | Hartford Athletic | - | Loudoun United | 2:1 | ||||
| 4. Round | 11/07/2021 | Loudoun United | - | Miami FC | 1:4 | ||||
| 4. Round | 18/07/2021 | Pittsburgh Riverhounds | - | Loudoun United | 1:0 | ||||
| 5. Round | 19/08/2021 | Loudoun United | - | Indy Eleven | 4:1 | ||||
| 5. Round | 24/08/2021 | Loudoun United | - | Tampa Bay Rowdies | 0:2 | ||||
| 6. Round | 09/09/2021 | Loudoun United | - | Charlotte Independence | 0:5 | ||||
| 6. Round | 12/09/2021 | Pittsburgh Riverhounds | - | Loudoun United | 5:0 | ||||
| 6. Round | 26/09/2021 | Miami FC | - | Loudoun United | 6:1 | ||||
| 7. Round | 14/10/2021 | Loudoun United | - | Hartford Athletic | 2:3 |  |
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| 7. Round | 21/10/2021 | New York RB II | - | Loudoun United | 3:0 |
USA