| 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 | ||||
| 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 | ||||
| 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 |
USA
Germany