| 5. Jornada | 18.07.2019 | North Carolina FC | - | Loudoun United | 3:0 | ||||
| 5. Jornada | 21.07.2019 | Indy Eleven | - | Loudoun United | 2:0 | ||||
| 5. Jornada | 29.07.2019 | Loudoun United | - | Louisville City FC | 3:0 | ||||
| 6. Jornada | 03.08.2019 | Atlanta United II | - | Loudoun United | 4:2 | ||||
| 6. Jornada | 10.08.2019 | Loudoun United | - | Charlotte Independence | 3:3 |  |
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| 6. Jornada | 15.08.2019 | Loudoun United | - | Charleston Battery | 1:2 | ||||
| 6. Jornada | 18.08.2019 | Loudoun United | - | Ottawa Fury | 1:3 | ||||
| 6. Jornada | 24.08.2019 | Pittsburgh Riverhounds | - | Loudoun United | 1:0 | ||||
| 6. Jornada | 29.08.2019 | Loudoun United | - | Birmingham Legion | 1:1 |  |
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| 7. Jornada | 01.09.2019 | Loudoun United | - | North Carolina FC | 4:0 | ||||
| 7. Jornada | 07.09.2019 | Hartford Athletic | - | Loudoun United | 5:1 | ||||
| 7. Jornada | 14.09.2019 | Loudoun United | - | Memphis 901 | 1:2 | ||||
| 7. Jornada | 19.09.2019 | Bethlehem Steel FC | - | Loudoun United | 5:2 |  |
Estados Unidos