| 1. Round | 17/03/2018 | North Carolina FC | - | Tampa Bay Rowdies | 1:3 | ||||
| 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 | 13/05/2018 | Richmond Kickers | - | Tampa Bay Rowdies | 1:0 | ||||
| 3. Round | 20/05/2018 | Tampa Bay Rowdies | - | Pittsburgh Riverhounds | 2:2 | ||||
| 3. Round | 26/05/2018 | Toronto FC 2 | - | Tampa Bay Rowdies | 2:4 |  |
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| 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 | |
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| 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 | ||||
| 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 | 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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