| 2. Round | 19/07/2020 | Philadelphia Union 2 | - | Pittsburgh Riverhounds | 0:6 |  |
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| 2. Round | 22/07/2020 | Pittsburgh Riverhounds | - | Indy Eleven | 0:1 | ||||
| 2. Round | 26/07/2020 | New York RB II | - | Pittsburgh Riverhounds | 2:1 | ||||
| 3. Round | 02/08/2020 | Pittsburgh Riverhounds | - | Philadelphia Union 2 | 4:0 | |
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| 3. Round | 09/08/2020 | Pittsburgh Riverhounds | - | New York RB II | 4:1 |  |
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| 3. Round | 16/08/2020 | Indy Eleven | - | Pittsburgh Riverhounds | 1:0 | |
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| 3. Round | 20/08/2020 | Loudoun United | - | Pittsburgh Riverhounds | 0:2 | |
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| 3. Round | 23/08/2020 | Pittsburgh Riverhounds | - | Saint Louis FC | 2:2 | ||||
| 3. Round | 29/08/2020 | Hartford Athletic | - | Pittsburgh Riverhounds | 0:3 | ||||
| 4. Round | 02/09/2020 | Pittsburgh Riverhounds | - | Loudoun United | 3:0 | ||||
| 4. Round | 05/09/2020 | New York RB II | - | Pittsburgh Riverhounds | 0:3 | ||||
| 4. Round | 19/09/2020 | Loudoun United | - | Pittsburgh Riverhounds | 0:1 | ||||
| 4. Round | 27/09/2020 | Pittsburgh Riverhounds | - | Hartford Athletic | 0:1 | |
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| 5. Round | 04/10/2020 | Pittsburgh Riverhounds | - | Philadelphia Union 2 | 2:1 |
Cape Verde