| 4. Round | 06/06/2019 | Swope Park Rangers | - | Loudoun United | 2:3 | ||||
| 4. Round | 16/06/2019 | Loudoun United | - | Indy Eleven | 1:2 |  |
|||
| 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 | ||||
| 5. Round | 29/07/2019 | Loudoun United | - | Louisville City FC | 3:0 | |
|||
| 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 | 18/08/2019 | Loudoun United | - | Ottawa Fury | 1:3 | ||||
| 6. Round | 24/08/2019 | Pittsburgh Riverhounds | - | Loudoun United | 1:0 | |
|||
| 7. Round | 01/09/2019 | Loudoun United | - | North Carolina FC | 4:0 | ||||
| 7. Round | 14/09/2019 | Loudoun United | - | Memphis 901 | 1:2 |  |
|||
| 7. Round | 26/09/2019 | Loudoun United | - | Swope Park Rangers | 4:1 | ||||
| 8. Round | 10/10/2019 | Loudoun United | - | Saint Louis FC | 4:3 | ||||
| 8. Round | 13/10/2019 | Charleston Battery | - | Loudoun United | 1:2 | ||||
| 8. Round | 20/10/2019 | Loudoun United | - | New York RB II | 7:3 |
USA
El Salvador