2. Round | 20/04/2019 | New York RB II | - | Loudoun United | 1:3 | ||||
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 |