1. Round | 03/07/2016 | Tampa Bay Rowdies | - | Jacksonville Armada | 1:1 | ||||
1. Round | 10/07/2016 | Carolina RailHawks | - | Tampa Bay Rowdies | 4:1 | ||||
1. Round | 17/07/2016 | Tampa Bay Rowdies | - | Puerto Rico FC | 3:0 | ||||
2. Round | 18/08/2016 | Minnesota United FC | - | Tampa Bay Rowdies | 2:0 | ||||
2. Round | 21/08/2016 | Tampa Bay Rowdies | - | FC Edmonton | 0:1 | ||||
2. Round | 28/08/2016 | Tampa Bay Rowdies | - | Rayo OKC | 2:0 | ||||
3. Round | 04/09/2016 | Indy Eleven | - | Tampa Bay Rowdies | 1:1 | ||||
3. Round | 11/09/2016 | Tampa Bay Rowdies | - | Puerto Rico FC | 0:0 | ||||
3. Round | 18/09/2016 | Tampa Bay Rowdies | - | Carolina RailHawks | 1:0 | ||||
3. Round | 25/09/2016 | Fort Lauderdale Strikers | - | Tampa Bay Rowdies | 1:4 | ||||
4. Round | 02/10/2016 | Tampa Bay Rowdies | - | Miami FC | 1:1 | ||||
4. Round | 23/10/2016 | Tampa Bay Rowdies | - | Ottawa Fury | 1:1 |