| 1. Round | 03/04/2016 | Tampa Bay Rowdies | - | Indy Eleven | 0:0 | ||||
| 2. Round | 10/04/2016 | Miami FC | - | Tampa Bay Rowdies | 1:1 | ||||
| 3. Round | 17/04/2016 | Tampa Bay Rowdies | - | FC Edmonton | 1:0 | ||||
| 4. Round | 24/04/2016 | Tampa Bay Rowdies | - | Carolina RailHawks | 1:3 | ||||
| 5. Round | 01/05/2016 | Fort Lauderdale Strikers | - | Tampa Bay Rowdies | 0:1 | ||||
| 7. Round | 15/05/2016 | Tampa Bay Rowdies | - | Rayo OKC | 1:1 | ||||
| 8. Round | 22/05/2016 | New York Cosmos | - | Tampa Bay Rowdies | 2:1 | ||||
| 9. Round | 29/05/2016 | Minnesota United FC | - | Tampa Bay Rowdies | 0:2 | ||||
| 10. Round | 05/06/2016 | Tampa Bay Rowdies | - | Ottawa Fury | 2:1 |  |
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| 11. Round | 11/06/2016 | Jacksonville Armada | - | Tampa Bay Rowdies | 1:1 |
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