| 2. Round | 09/04/2023 | Colorado Springs Switchbacks | - | Pittsburgh Riverhounds | 1:0 | ||||
| 2. Round | 16/04/2023 | Pittsburgh Riverhounds | - | Rio Grande Valley FC | 2:0 | ||||
| 4. Round | 25/06/2023 | Pittsburgh Riverhounds | - | San Diego Loyal | 2:1 |  |
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| 5. Round | 02/07/2023 | Pittsburgh Riverhounds | - | Louisville City FC | 0:0 | ||||
| 5. Round | 09/07/2023 | Pittsburgh Riverhounds | - | Sacramento Republic | 0:0 | ||||
| 5. Round | 13/07/2023 | Louisville City FC | - | Pittsburgh Riverhounds | 0:1 | ||||
| 6. Round | 27/08/2023 | San Antonio FC | - | Pittsburgh Riverhounds | 0:0 | ||||
| 7. Round | 10/09/2023 | Pittsburgh Riverhounds | - | Loudoun United | 3:1 | ||||
| 7. Round | 17/09/2023 | Miami FC | - | Pittsburgh Riverhounds | 1:2 |
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