| 5. Round | 01/05/2016 | Rayo OKC | - | Indy Eleven | 1:2 |  |
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| 6. Round | 08/05/2016 | Indy Eleven | - | FC Edmonton | 1:1 | ||||
| 7. Round | 15/05/2016 | Fort Lauderdale Strikers | - | Indy Eleven | 0:0 | ||||
| 8. Round | 22/05/2016 | Indy Eleven | - | Minnesota United FC | 4:2 |  |
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| 9. Round | 29/05/2016 | Jacksonville Armada | - | Indy Eleven | 1:1 | ||||
| 10. Round | 05/06/2016 | Miami FC | - | Indy Eleven | 0:0 | ||||
| 11. Round | 12/06/2016 | Indy Eleven | - | Carolina RailHawks | 4:1 |
Jamaica