| 1. Round | 03/07/2016 | Puerto Rico FC | - | Indy Eleven | 1:1 | ||||
| 1. Round | 10/07/2016 | Indy Eleven | - | Minnesota United FC | 1:0 | ||||
| 1. Round | 14/07/2016 | Indy Eleven | - | Fort Lauderdale Strikers | 3:0 | ||||
| 1. Round | 24/07/2016 | Indy Eleven | - | FC Edmonton | 1:0 | ||||
| 1. Round | 31/07/2016 | Miami FC | - | Indy Eleven | 2:1 | ||||
| 2. Round | 04/08/2016 | Indy Eleven | - | Jacksonville Armada | 5:2 | ||||
| 2. Round | 07/08/2016 | Indy Eleven | - | Ottawa Fury | 1:0 | ||||
| 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 | ||||
| 4. Round | 30/10/2016 | Rayo OKC | - | Indy Eleven | 2:1 |  |
USA