| 1. Round | 15/03/2019 | Charlotte Independence | - | Indy Eleven | 2:3 | ||||
| 3. Round | 19/05/2019 | Indy Eleven | - | Charleston Battery | 1:0 | ||||
| 3. Round | 26/05/2019 | Indy Eleven | - | Nashville SC | 0:0 | ||||
| 4. Round | 02/06/2019 | Indy Eleven | - | Pittsburgh Riverhounds | 2:1 | ||||
| 4. Round | 27/06/2019 | Indy Eleven | - | Birmingham Legion | 3:0 | ||||
| 4. Round | 30/06/2019 | Indy Eleven | - | Louisville City FC | 1:1 |  |
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| 5. Round | 21/07/2019 | Indy Eleven | - | Loudoun United | 2:0 | ||||
| 5. Round | 28/07/2019 | Nashville SC | - | Indy Eleven | 2:0 | ||||
| 6. Round | 04/08/2019 | North Carolina FC | - | Indy Eleven | 1:2 | ||||
| 6. Round | 18/08/2019 | Indy Eleven | - | Saint Louis FC | 2:1 | ||||
| 6. Round | 25/08/2019 | Indy Eleven | - | Charlotte Independence | 3:1 | ||||
| 6. Round | 31/08/2019 | Louisville City FC | - | Indy Eleven | 1:1 | ||||
| 7. Round | 05/09/2019 | Indy Eleven | - | New York RB II | 1:0 |
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