1. Round | 31/07/2016 | Miami FC | - | Indy Eleven | 2:1 | ||||
3. Round | 18/09/2016 | Indy Eleven | - | Miami FC | 2:1 | ||||
3. Round | 25/09/2016 | Indy Eleven | - | New York Cosmos | 3:0 | ||||
4. Round | 02/10/2016 | FC Edmonton | - | Indy Eleven | 2:1 | ||||
4. Round | 13/10/2016 | Jacksonville Armada | - | Indy Eleven | 0:0 | ||||
4. Round | 16/10/2016 | Indy Eleven | - | Carolina RailHawks | 3:0 | ||||
4. Round | 20/10/2016 | Tampa Bay Rowdies | - | Indy Eleven | 2:3 | ||||
4. Round | 23/10/2016 | Indy Eleven | - | Puerto Rico FC | 3:0 |