| 1. Round | 17/03/2018 | North Carolina FC | - | Tampa Bay Rowdies | 1:3 | ||||
| 1. Round | 24/03/2018 | Tampa Bay Rowdies | - | Bethlehem Steel FC | 2:0 | ||||
| 1. Round | 31/03/2018 | Louisville City FC | - | Tampa Bay Rowdies | 1:0 | ||||
| 2. Round | 08/04/2018 | Tampa Bay Rowdies | - | Ottawa Fury | 5:0 | ||||
| 2. Round | 14/04/2018 | New York RB II | - | Tampa Bay Rowdies | 5:0 | ||||
| 2. Round | 22/04/2018 | Tampa Bay Rowdies | - | Real Monarchs SLC | 2:0 | ||||
| 2. Round | 29/04/2018 | Charleston Battery | - | Tampa Bay Rowdies | 1:0 | ||||
| 3. Round | 05/05/2018 | Penn FC | - | Tampa Bay Rowdies | 3:0 | ||||
| 3. Round | 13/05/2018 | Richmond Kickers | - | Tampa Bay Rowdies | 1:0 | ||||
| 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 |  |
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| 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 |
USA