| 4. Round | 29/06/2019 | Loudoun United | - | Atlanta United II | 2:1 |  |
|||
| 5. Round | 07/07/2019 | Saint Louis FC | - | Loudoun United | 2:2 | ||||
| 5. Round | 18/07/2019 | North Carolina FC | - | Loudoun United | 3:0 | ||||
| 5. Round | 21/07/2019 | Indy Eleven | - | Loudoun United | 2:0 | ||||
| 6. Round | 03/08/2019 | Atlanta United II | - | Loudoun United | 4:2 | ||||
| 6. Round | 10/08/2019 | Loudoun United | - | Charlotte Independence | 3:3 | ||||
| 6. Round | 24/08/2019 | Pittsburgh Riverhounds | - | Loudoun United | 1:0 | ||||
| 6. Round | 29/08/2019 | Loudoun United | - | Birmingham Legion | 1:1 | ||||
| 8. Round | 05/10/2019 | Loudoun United | - | Tampa Bay Rowdies | 2:0 |
USA