| 4. Round | 16/06/2019 | Loudoun United | - | Indy Eleven | 1:2 | ||||
| 4. Round | 23/06/2019 | Indy Eleven | - | Atlanta United II | 1:0 | ||||
| 4. Round | 27/06/2019 | Indy Eleven | - | Birmingham Legion | 3:0 | ||||
| 4. Round | 30/06/2019 | Indy Eleven | - | Louisville City FC | 1:1 | ||||
| 8. Round | 03/10/2019 | Ottawa Fury | - | Indy Eleven | 1:0 | ||||
| 8. Round | 06/10/2019 | Indy Eleven | - | Memphis 901 | 3:0 | ||||
| 8. Round | 13/10/2019 | Tampa Bay Rowdies | - | Indy Eleven | 1:1 | ||||
| 8. Round | 17/10/2019 | Indy Eleven | - | Swope Park Rangers | 2:1 |
USA