1. Round | 30/03/2019 | Tampa Bay Rowdies | - | Loudoun United | 0:0 | ||||
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 | 04/05/2019 | Loudoun United | - | Bethlehem Steel FC | 3:3 | ||||
4. Round | 16/06/2019 | Loudoun United | - | Indy Eleven | 1:2 | ||||
4. Round | 29/06/2019 | Loudoun United | - | Atlanta United II | 2:1 |