| 1. Round | 03/07/2016 | Tampa Bay Rowdies | - | Jacksonville Armada | 1:1 |  |
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| 1. Round | 17/07/2016 | Miami FC | - | Jacksonville Armada | 1:0 | ||||
| 1. Round | 31/07/2016 | Fort Lauderdale Strikers | - | Jacksonville Armada | 1:0 | |
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| 2. Round | 04/08/2016 | Indy Eleven | - | Jacksonville Armada | 5:2 | |
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| 2. Round | 07/08/2016 | Jacksonville Armada | - | Carolina RailHawks | 2:2 | ||||
| 2. Round | 18/08/2016 | Jacksonville Armada | - | Fort Lauderdale Strikers | 1:1 | ||||
| 2. Round | 20/08/2016 | Jacksonville Armada | - | Minnesota United FC | 0:0 | ||||
| 3. Round | 04/09/2016 | Carolina RailHawks | - | Jacksonville Armada | 1:0 | ||||
| 3. Round | 29/09/2016 | Jacksonville Armada | - | FC Edmonton | 0:0 | |
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| 4. Round | 13/10/2016 | Jacksonville Armada | - | Indy Eleven | 0:0 | ||||
| 4. Round | 20/10/2016 | Jacksonville Armada | - | Miami FC | 3:2 |  |
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| 4. Round | 23/10/2016 | FC Edmonton | - | Jacksonville Armada | 1:0 |
Argentina
Italy