| 1. Round | 10/03/2019 | Nashville SC | - | Loudoun United | 2:0 | ||||
| 1. Round | 17/03/2019 | Memphis 901 | - | Loudoun United | 1:1 | ||||
| 2. Round | 13/04/2019 | Ottawa Fury | - | Loudoun United | 2:0 |  |
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| 2. Round | 28/04/2019 | Birmingham Legion | - | Loudoun United | 1:0 | ||||
| 3. Round | 12/05/2019 | Charlotte Independence | - | Loudoun United | 1:3 | |
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| 3. Round | 19/05/2019 | Loudoun United | - | Hartford Athletic | 1:2 | ||||
| 4. Round | 16/06/2019 | Loudoun United | - | Indy Eleven | 1:2 | ||||
| 5. Round | 18/07/2019 | North Carolina FC | - | Loudoun United | 3:0 | ||||
| 8. Round | 10/10/2019 | Loudoun United | - | Saint Louis FC | 4:3 |  |
Honduras