| 6. Round | 11/08/2019 | Pittsburgh Riverhounds | - | Swope Park Rangers | 3:2 | ||||
| 7. Round | 01/09/2019 | Bethlehem Steel FC | - | Swope Park Rangers | 2:0 |  |
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| 7. Round | 08/09/2019 | Memphis 901 | - | Swope Park Rangers | 4:2 | ||||
| 7. Round | 12/09/2019 | Swope Park Rangers | - | Charleston Battery | 0:0 | ||||
| 7. Round | 14/09/2019 | Swope Park Rangers | - | North Carolina FC | 1:0 | ||||
| 8. Round | 06/10/2019 | Hartford Athletic | - | Swope Park Rangers | 2:2 | ||||
| 8. Round | 09/10/2019 | Swope Park Rangers | - | Ottawa Fury | 1:2 |  |
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| 8. Round | 17/10/2019 | Indy Eleven | - | Swope Park Rangers | 2:1 |
Jamaica