| 1. Round | 10/03/2019 | Nashville SC | - | Loudoun United | 2:0 | ||||
| 1. Round | 17/03/2019 | Memphis 901 | - | Loudoun United | 1:1 | ||||
| 2. Round | 20/04/2019 | New York RB II | - | Loudoun United | 1:3 | ||||
| 3. Round | 12/05/2019 | Charlotte Independence | - | Loudoun United | 1:3 | ||||
| 4. Round | 06/06/2019 | Swope Park Rangers | - | Loudoun United | 2:3 | ||||
| 4. Round | 09/06/2019 | Louisville City FC | - | Loudoun United | 2:1 | ||||
| 5. Round | 18/07/2019 | North Carolina FC | - | Loudoun United | 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 | 29/08/2019 | Loudoun United | - | Birmingham Legion | 1:1 | ||||
| 7. Round | 01/09/2019 | Loudoun United | - | North Carolina FC | 4:0 | ||||
| 7. Round | 07/09/2019 | Hartford Athletic | - | Loudoun United | 5:1 | ||||
| 7. Round | 26/09/2019 | Loudoun United | - | Swope Park Rangers | 4:1 | ||||
| 8. Round | 02/10/2019 | Loudoun United | - | Pittsburgh Riverhounds | 1:2 | ||||
| 8. Round | 20/10/2019 | Loudoun United | - | New York RB II | 7:3 |
USA