2. Round | 01/09/2016 | New York Cosmos | - | Indy Eleven | 3:0 | ||||
3. Round | 04/09/2016 | Indy Eleven | - | Tampa Bay Rowdies | 1:1 | ||||
3. Round | 11/09/2016 | Fort Lauderdale Strikers | - | Indy Eleven | 2:1 | ||||
3. Round | 18/09/2016 | Indy Eleven | - | Miami FC | 2:1 | ||||
4. Round | 20/10/2016 | Tampa Bay Rowdies | - | Indy Eleven | 2:3 | ||||
4. Round | 30/10/2016 | Rayo OKC | - | Indy Eleven | 2:1 |