| 1. Round | 09/03/2019 | Saint Louis FC | - | Indy Eleven | 2:1 | ||||
| 1. Round | 15/03/2019 | Charlotte Independence | - | Indy Eleven | 2:3 | ||||
| 3. Round | 05/05/2019 | Indy Eleven | - | North Carolina FC | 0:0 | ||||
| 3. Round | 26/05/2019 | Indy Eleven | - | Nashville SC | 0:0 | ||||
| 4. Round | 02/06/2019 | Indy Eleven | - | Pittsburgh Riverhounds | 2:1 |
USA