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 | 28/04/2019 | Birmingham Legion | - | Loudoun United | 1:0 | ||||
3. Round | 04/05/2019 | Loudoun United | - | Bethlehem Steel FC | 3:3 | ||||
3. Round | 19/05/2019 | Loudoun United | - | Hartford Athletic | 1:2 | ||||
4. Round | 29/06/2019 | Loudoun United | - | Atlanta United II | 2:1 | ||||
5. Round | 07/07/2019 | Saint Louis FC | - | Loudoun United | 2:2 | ||||
5. Round | 21/07/2019 | Indy Eleven | - | Loudoun United | 2:0 | ||||
5. Round | 29/07/2019 | Loudoun United | - | Louisville City FC | 3:0 | ||||
6. Round | 18/08/2019 | Loudoun United | - | Ottawa Fury | 1:3 | ||||
6. Round | 24/08/2019 | Pittsburgh Riverhounds | - | Loudoun United | 1:0 | ||||
7. Round | 14/09/2019 | Loudoun United | - | Memphis 901 | 1:2 | ||||
7. Round | 19/09/2019 | Bethlehem Steel FC | - | Loudoun United | 5:2 | ||||
7. Round | 29/09/2019 | Loudoun United | - | Nashville SC | 0:2 | ||||
8. Round | 05/10/2019 | Loudoun United | - | Tampa Bay Rowdies | 2:0 | ||||
8. Round | 10/10/2019 | Loudoun United | - | Saint Louis FC | 4:3 |