| 3. Round | 05/05/2019 | Charleston Battery | - | Pittsburgh Riverhounds | 2:2 | ||||
| 4. Round | 16/06/2019 | Atlanta United II | - | Pittsburgh Riverhounds | 0:5 | ||||
| 4. Round | 30/06/2019 | Pittsburgh Riverhounds | - | Birmingham Legion | 4:1 | ||||
| 5. Round | 05/07/2019 | Pittsburgh Riverhounds | - | Bethlehem Steel FC | 1:0 | ||||
| 5. Round | 21/07/2019 | Pittsburgh Riverhounds | - | North Carolina FC | 1:0 | ||||
| 5. Round | 27/07/2019 | Hartford Athletic | - | Pittsburgh Riverhounds | 2:4 | ||||
| 6. Round | 11/08/2019 | Pittsburgh Riverhounds | - | Swope Park Rangers | 3:2 | ||||
| 6. Round | 18/08/2019 | North Carolina FC | - | Pittsburgh Riverhounds | 5:0 | ||||
| 6. Round | 24/08/2019 | Pittsburgh Riverhounds | - | Loudoun United | 1:0 | ||||
| 6. Round | 31/08/2019 | Ottawa Fury | - | Pittsburgh Riverhounds | 0:4 |  |
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| 7. Round | 15/09/2019 | Pittsburgh Riverhounds | - | Charleston Battery | 1:0 | ||||
| 7. Round | 25/09/2019 | Memphis 901 | - | Pittsburgh Riverhounds | 0:1 | ||||
| 8. Round | 02/10/2019 | Loudoun United | - | Pittsburgh Riverhounds | 1:2 |
Ethiopia