2. Round | 03/05/2021 | Miami FC | - | Loudoun United | 2:1 | ||||
2. Round | 19/05/2021 | Loudoun United | - | New York RB II | 1:2 | ||||
2. Round | 30/05/2021 | New Mexico United | - | Loudoun United | 0:1 | ||||
3. Round | 03/06/2021 | Loudoun United | - | Pittsburgh Riverhounds | 2:3 | ||||
3. Round | 12/06/2021 | Tampa Bay Rowdies | - | Loudoun United | 2:1 | ||||
3. Round | 27/06/2021 | Charleston Battery | - | Loudoun United | 3:0 | ||||
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 | 26/09/2021 | Miami FC | - | Loudoun United | 6:1 |