1. Round | 17/03/2019 | Memphis 901 | - | Loudoun United | 1:1 | ||||
1. Round | 30/03/2019 | Tampa Bay Rowdies | - | Loudoun United | 0:0 | ||||
2. Round | 13/04/2019 | Ottawa Fury | - | Loudoun United | 2:0 | ||||
2. Round | 20/04/2019 | New York RB II | - | Loudoun United | 1:3 | ||||
2. Round | 28/04/2019 | Birmingham Legion | - | Loudoun United | 1:0 | ||||
3. Round | 12/05/2019 | Charlotte Independence | - | Loudoun United | 1:3 | ||||
3. Round | 19/05/2019 | Loudoun United | - | Hartford Athletic | 1:2 | ||||
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 | 18/07/2019 | North Carolina FC | - | Loudoun United | 3:0 | ||||
5. Round | 29/07/2019 | Loudoun United | - | Louisville City FC | 3:0 | ||||
6. Round | 18/08/2019 | Loudoun United | - | Ottawa Fury | 1:3 |