| 5. Round | 15/07/2018 | FC Cincinnati | - | Tampa Bay Rowdies | 2:0 | ||||
| 5. Round | 22/07/2018 | Tampa Bay Rowdies | - | Indy Eleven | 3:1 | ||||
| 5. Round | 29/07/2018 | Tampa Bay Rowdies | - | New York RB II | 2:2 | ||||
| 6. Round | 04/08/2018 | Ottawa Fury | - | Tampa Bay Rowdies | 2:0 | ||||
| 6. Round | 09/08/2018 | Tampa Bay Rowdies | - | Charleston Battery | 0:0 | ||||
| 6. Round | 12/08/2018 | Tampa Bay Rowdies | - | North Carolina FC | 0:2 | ||||
| 6. Round | 26/08/2018 | Tampa Bay Rowdies | - | FC Cincinnati | 1:2 |  |
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| 7. Round | 02/09/2018 | North Carolina FC | - | Tampa Bay Rowdies | 0:3 | ||||
| 7. Round | 09/09/2018 | Charleston Battery | - | Tampa Bay Rowdies | 1:0 | ||||
| 7. Round | 16/09/2018 | Tampa Bay Rowdies | - | Atlanta United II | 1:0 | ||||
| 7. Round | 19/09/2018 | Nashville SC | - | Tampa Bay Rowdies | 1:2 | ||||
| 7. Round | 23/09/2018 | Tampa Bay Rowdies | - | Richmond Kickers | 3:0 | ||||
| 7. Round | 27/09/2018 | Indy Eleven | - | Tampa Bay Rowdies | 2:0 | ||||
| 8. Round | 04/10/2018 | Atlanta United II | - | Tampa Bay Rowdies | 1:1 | ||||
| 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 |
Ghana