1. Round | 10/07/2016 | Jacksonville Armada | - | Puerto Rico FC | 2:1 | ||||
1. Round | 14/07/2016 | Rayo OKC | - | Puerto Rico FC | 2:2 | ||||
3. Round | 04/09/2016 | Puerto Rico FC | - | Miami FC | 0:3 | ||||
3. Round | 11/09/2016 | Tampa Bay Rowdies | - | Puerto Rico FC | 0:0 | ||||
3. Round | 18/09/2016 | Puerto Rico FC | - | Jacksonville Armada | 3:3 |