| 2. Round | 13/04/2019 | Ottawa Fury | - | Loudoun United | 2:0 | ||||
| 2. Round | 28/04/2019 | Birmingham Legion | - | Loudoun United | 1:0 | ||||
| 3. Round | 04/05/2019 | Loudoun United | - | Bethlehem Steel FC | 3:3 | ||||
| 3. Round | 12/05/2019 | Charlotte Independence | - | Loudoun United | 1:3 | ||||
| 3. Round | 19/05/2019 | Loudoun United | - | Hartford Athletic | 1:2 |  |
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| 4. Round | 06/06/2019 | Swope Park Rangers | - | Loudoun United | 2:3 |
USA