| 3. Round | 20/05/2018 | Tampa Bay Rowdies | - | Pittsburgh Riverhounds | 2:2 | ||||
| 4. Round | 03/06/2018 | Tampa Bay Rowdies | - | Atlanta United II | 0:0 | ||||
| 4. Round | 10/06/2018 | Tampa Bay Rowdies | - | Nashville SC | 1:1 | ||||
| 4. Round | 23/06/2018 | Tampa Bay Rowdies | - | Penn FC | 1:2 | ||||
| 4. Round | 28/06/2018 | Charlotte Independence | - | Tampa Bay Rowdies | 2:2 | ||||
| 5. Round | 08/07/2018 | Tampa Bay Rowdies | - | Louisville City FC | 1:2 | ||||
| 6. Round | 04/08/2018 | Ottawa Fury | - | Tampa Bay Rowdies | 2:0 | ||||
| 7. Round | 09/09/2018 | Charleston Battery | - | Tampa Bay Rowdies | 1:0 | ||||
| 7. Round | 27/09/2018 | Indy Eleven | - | Tampa Bay Rowdies | 2:0 | ||||
| 8. Round | 07/10/2018 | Tampa Bay Rowdies | - | Charlotte Independence | 1:2 | ||||
| 8. Round | 14/10/2018 | Bethlehem Steel FC | - | Tampa Bay Rowdies | 1:0 |
USA