| 7. Round | 23/09/2018 | Tampa Bay Rowdies | - | Richmond Kickers | 3:0 |  |
 |
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| 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 |
USA