| 4. Round | 18/07/2021 | Pittsburgh Riverhounds | - | Loudoun United | 1:0 | ||||
| 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 |  |
|||
| 5. Round | 24/08/2021 | Loudoun United | - | Tampa Bay Rowdies | 0:2 | |
|||
| 6. Round | 05/09/2021 | Rio Grande Valley FC | - | Loudoun United | 1:1 | |
|||
| 6. Round | 12/09/2021 | Pittsburgh Riverhounds | - | Loudoun United | 5:0 | ||||
| 7. Round | 01/10/2021 | New York RB II | - | Loudoun United | 3:3 | ||||
| 7. Round | 04/10/2021 | Charlotte Independence | - | Loudoun United | 5:1 |
El Salvador
USA