| 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 | 17/07/2016 | Minnesota United FC | - | Indy Eleven | 2:0 | ||||
| 1. Round | 24/07/2016 | Indy Eleven | - | FC Edmonton | 1:0 | ||||
| 1. Round | 31/07/2016 | Miami FC | - | Indy Eleven | 2:1 | ||||
| 2. Round | 07/08/2016 | Indy Eleven | - | Ottawa Fury | 1:0 | ||||
| 2. Round | 21/08/2016 | Carolina RailHawks | - | Indy Eleven | 3:2 | ||||
| 2. Round | 01/09/2016 | New York Cosmos | - | Indy Eleven | 3:0 |  |
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| 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 |
USA