| 1. Round | 10/07/2016 | Jacksonville Armada | - | Puerto Rico FC | 2:1 | ||||
| 1. Round | 31/07/2016 | Fort Lauderdale Strikers | - | Jacksonville Armada | 1:0 | ||||
| 2. Round | 04/08/2016 | Indy Eleven | - | Jacksonville Armada | 5:2 | ||||
| 2. Round | 07/08/2016 | Jacksonville Armada | - | Carolina RailHawks | 2:2 | ||||
| 2. Round | 13/08/2016 | Ottawa Fury | - | Jacksonville Armada | 1:2 | ||||
| 2. Round | 18/08/2016 | Jacksonville Armada | - | Fort Lauderdale Strikers | 1:1 | ||||
| 3. Round | 04/09/2016 | Carolina RailHawks | - | Jacksonville Armada | 1:0 | ||||
| 3. Round | 12/09/2016 | Rayo OKC | - | Jacksonville Armada | 3:2 | ||||
| 3. Round | 25/09/2016 | Jacksonville Armada | - | Rayo OKC | 1:1 | ||||
| 4. Round | 02/10/2016 | Minnesota United FC | - | Jacksonville Armada | 0:1 |  |
England