| 1. Round | 09/03/2019 | New York RB II | - | Swope Park Rangers | 3:1 | ||||
| 6. Round | 04/08/2019 | Swope Park Rangers | - | Nashville SC | 0:2 | ||||
| 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 | ||||
| 6. Round | 25/08/2019 | Swope Park Rangers | - | New York RB II | 1:5 | ||||
| 7. Round | 01/09/2019 | Bethlehem Steel FC | - | Swope Park Rangers | 2:0 | ||||
| 7. Round | 12/09/2019 | Swope Park Rangers | - | Charleston Battery | 0:0 |  |
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| 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 | |
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| 7. Round | 26/09/2019 | Loudoun United | - | Swope Park Rangers | 4:1 | ||||
| 8. Round | 01/10/2019 | Swope Park Rangers | - | Birmingham Legion | 3:1 | ||||
| 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 | ||||
| 8. Round | 17/10/2019 | Indy Eleven | - | Swope Park Rangers | 2:1 |
USA