| 1. Round | 09/03/2019 | Saint Louis FC | - | Indy Eleven | 2:1 | ||||
| 1. Round | 15/03/2019 | Charlotte Independence | - | Indy Eleven | 2:3 | ||||
| 1. Round | 30/03/2019 | Indy Eleven | - | Hartford Athletic | 1:0 | ||||
| 6. Round | 18/08/2019 | Indy Eleven | - | Saint Louis FC | 2:1 | ||||
| 7. Round | 08/09/2019 | Charleston Battery | - | Indy Eleven | 1:0 | ||||
| 7. Round | 12/09/2019 | Indy Eleven | - | Ottawa Fury | 2:0 | ||||
| 7. Round | 21/09/2019 | Birmingham Legion | - | Indy Eleven | 1:0 | ||||
| 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 | 03/10/2019 | Ottawa Fury | - | Indy Eleven | 1:0 | ||||
| 8. Round | 13/10/2019 | Tampa Bay Rowdies | - | Indy Eleven | 1:1 |
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