| 2. Round | 03/05/2021 | Miami FC | - | Loudoun United | 2:1 | ||||
| 4. Round | 28/07/2021 | Loudoun United | - | Charleston Battery | 3:5 | ||||
| 4. Round | 01/08/2021 | Loudoun United | - | Colorado Springs Switchbacks | 1:3 |  |
|||
| 5. Round | 07/08/2021 | Loudoun United | - | Charlotte Independence | 0:0 | ||||
| 5. Round | 14/08/2021 | Charleston Battery | - | Loudoun United | 1:0 | ||||
| 5. Round | 19/08/2021 | Loudoun United | - | Indy Eleven | 4:1 | ||||
| 6. Round | 09/09/2021 | Loudoun United | - | Charlotte Independence | 0:5 | ||||
| 7. Round | 14/10/2021 | Loudoun United | - | Hartford Athletic | 2:3 | |
USA