| 1. Round | 15/03/2019 | Charlotte Independence | - | Indy Eleven | 2:3 | ||||
| 1. Round | 30/03/2019 | Indy Eleven | - | Hartford Athletic | 1:0 | ||||
| 2. Round | 16/04/2019 | Swope Park Rangers | - | Indy Eleven | 1:3 | ||||
| 2. Round | 20/04/2019 | Bethlehem Steel FC | - | Indy Eleven | 0:3 | ||||
| 3. Round | 02/05/2019 | Indy Eleven | - | Tampa Bay Rowdies | 0:0 | ||||
| 3. Round | 05/05/2019 | Indy Eleven | - | North Carolina FC | 0:0 |  |
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| 4. Round | 02/06/2019 | Indy Eleven | - | Pittsburgh Riverhounds | 2:1 | ||||
| 4. Round | 09/06/2019 | Memphis 901 | - | Indy Eleven | 0:3 | ||||
| 4. Round | 23/06/2019 | Indy Eleven | - | Atlanta United II | 1:0 |  |
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| 4. Round | 27/06/2019 | Indy Eleven | - | Birmingham Legion | 3:0 | ||||
| 4. Round | 30/06/2019 | Indy Eleven | - | Louisville City FC | 1:1 | ||||
| 5. Round | 13/07/2019 | Hartford Athletic | - | Indy Eleven | 2:1 | ||||
| 5. Round | 21/07/2019 | Indy Eleven | - | Loudoun United | 2:0 | ||||
| 5. Round | 28/07/2019 | Nashville SC | - | Indy Eleven | 2:0 | ||||
| 8. Round | 03/10/2019 | Ottawa Fury | - | Indy Eleven | 1:0 |
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