| 2. Round | 03/05/2021 | Miami FC | - | Loudoun United | 2:1 | ||||
| 2. Round | 19/05/2021 | Loudoun United | - | New York RB II | 1:2 | ||||
| 3. Round | 03/06/2021 | Loudoun United | - | Pittsburgh Riverhounds | 2:3 | ||||
| 3. Round | 09/06/2021 | Loudoun United | - | Charleston Battery | 0:1 | ||||
| 3. Round | 12/06/2021 | Tampa Bay Rowdies | - | Loudoun United | 2:1 | ||||
| 3. Round | 20/06/2021 | Hartford Athletic | - | Loudoun United | 2:1 | ||||
| 4. Round | 04/07/2021 | Loudoun United | - | Hartford Athletic | 0:2 | ||||
| 4. Round | 11/07/2021 | Loudoun United | - | Miami FC | 1:4 | ||||
| 4. Round | 18/07/2021 | Pittsburgh Riverhounds | - | Loudoun United | 1:0 | ||||
| 4. Round | 25/07/2021 | Tampa Bay Rowdies | - | Loudoun United | 3:1 | ||||
| 5. Round | 14/08/2021 | Charleston Battery | - | Loudoun United | 1:0 | ||||
| 5. Round | 19/08/2021 | Loudoun United | - | Indy Eleven | 4:1 | ||||
| 6. Round | 12/09/2021 | Pittsburgh Riverhounds | - | Loudoun United | 5:0 | ||||
| 6. Round | 26/09/2021 | Miami FC | - | Loudoun United | 6:1 | ||||
| 7. Round | 01/10/2021 | New York RB II | - | Loudoun United | 3:3 |
Canada