| 3. Round | 07/05/2019 | Swope Park Rangers | - | Louisville City FC | 3:2 | ||||
| 3. Round | 19/05/2019 | Swope Park Rangers | - | Atlanta United II | 1:1 | ||||
| 4. Round | 06/06/2019 | Swope Park Rangers | - | Loudoun United | 2:3 | ||||
| 4. Round | 30/06/2019 | Swope Park Rangers | - | Saint Louis FC | 2:1 | ||||
| 5. Round | 21/07/2019 | Ottawa Fury | - | Swope Park Rangers | 4:0 | ||||
| 6. Round | 11/08/2019 | Pittsburgh Riverhounds | - | Swope Park Rangers | 3:2 | ||||
| 6. Round | 17/08/2019 | Atlanta United II | - | Swope Park Rangers | 2:1 | ||||
| 7. Round | 01/09/2019 | Bethlehem Steel FC | - | Swope Park Rangers | 2:0 | ||||
| 7. Round | 08/09/2019 | Memphis 901 | - | Swope Park Rangers | 4:2 | ||||
| 7. Round | 14/09/2019 | Swope Park Rangers | - | North Carolina FC | 1:0 | ||||
| 7. Round | 22/09/2019 | Charlotte Independence | - | Swope Park Rangers | 0:3 | ||||
| 8. Round | 06/10/2019 | Hartford Athletic | - | Swope Park Rangers | 2:2 | ||||
| 8. Round | 09/10/2019 | Swope Park Rangers | - | Ottawa Fury | 1:2 | ||||
| 8. Round | 13/10/2019 | Louisville City FC | - | Swope Park Rangers | 8:3 |
USA
Palestine