| 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 | 08/09/2019 | Charleston Battery | - | Indy Eleven | 1:0 |  |
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| 7. Round | 26/09/2019 | Atlanta United II | - | Indy Eleven | 2:1 | ||||
| 7. Round | 29/09/2019 | Pittsburgh Riverhounds | - | Indy Eleven | 3:0 | ||||
| 8. Round | 06/10/2019 | Indy Eleven | - | Memphis 901 | 3:0 |
Brazil