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 | 28/07/2016 | Rayo OKC | - | Tampa Bay Rowdies | 1:0 | ||||
1. Round | 31/07/2016 | Ottawa Fury | - | Tampa Bay Rowdies | 2:0 | ||||
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 | 20/10/2016 | Tampa Bay Rowdies | - | Indy Eleven | 2:3 |