1. Round | 03/07/2016 | Tampa Bay Rowdies | - | Jacksonville Armada | 1:1 | ||||
2. Round | 07/08/2016 | Tampa Bay Rowdies | - | Fort Lauderdale Strikers | 2:1 | ||||
2. Round | 14/08/2016 | New York Cosmos | - | Tampa Bay Rowdies | 3:2 | ||||
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 | ||||
4. Round | 02/10/2016 | Tampa Bay Rowdies | - | Miami FC | 1:1 | ||||
4. Round | 06/10/2016 | Tampa Bay Rowdies | - | Minnesota United FC | 2:2 | ||||
4. Round | 09/10/2016 | FC Edmonton | - | Tampa Bay Rowdies | 1:0 | ||||
4. Round | 15/10/2016 | Miami FC | - | Tampa Bay Rowdies | 2:2 | ||||
4. Round | 20/10/2016 | Tampa Bay Rowdies | - | Indy Eleven | 2:3 | ||||
4. Round | 23/10/2016 | Tampa Bay Rowdies | - | Ottawa Fury | 1:1 | ||||
4. Round | 30/10/2016 | Jacksonville Armada | - | Tampa Bay Rowdies | 3:2 |