| 1. Round | 24/03/2018 | Nashville SC | - | Pittsburgh Riverhounds | 0:0 | ||||
| 1. Round | 01/04/2018 | Pittsburgh Riverhounds | - | Penn FC | 0:0 | ||||
| 2. Round | 15/04/2018 | Pittsburgh Riverhounds | - | Ottawa Fury | 1:0 | ||||
| 3. Round | 05/05/2018 | Toronto FC 2 | - | Pittsburgh Riverhounds | 1:2 | ||||
| 3. Round | 12/05/2018 | Pittsburgh Riverhounds | - | Indy Eleven | 0:0 | ||||
| 3. Round | 20/05/2018 | Tampa Bay Rowdies | - | Pittsburgh Riverhounds | 2:2 | ||||
| 3. Round | 27/05/2018 | Pittsburgh Riverhounds | - | Penn FC | 0:0 | ||||
| 3. Round | 31/05/2018 | Pittsburgh Riverhounds | - | Nashville SC | 0:1 | ||||
| 4. Round | 24/06/2018 | Charleston Battery | - | Pittsburgh Riverhounds | 0:0 | ||||
| 7. Round | 08/09/2018 | Pittsburgh Riverhounds | - | Bethlehem Steel FC | 4:1 | ||||
| 7. Round | 16/09/2018 | Pittsburgh Riverhounds | - | Louisville City FC | 2:2 | ||||
| 8. Round | 07/10/2018 | Pittsburgh Riverhounds | - | FC Cincinnati | 0:0 | ||||
| 8. Round | 10/10/2018 | Atlanta United II | - | Pittsburgh Riverhounds | 1:1 | ||||
| 8. Round | 14/10/2018 | New York RB II | - | Pittsburgh Riverhounds | 2:1 |
England