| 1. Round | 12/03/2023 | Tampa Bay Rowdies | - | Indy Eleven | 1:1 | ||||
| 1. Round | 25/03/2023 | Detroit City FC | - | Indy Eleven | 0:1 |  |
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| 2. Round | 02/04/2023 | Indy Eleven | - | Las Vegas Lights FC | 0:0 |  |
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| 2. Round | 09/04/2023 | Indy Eleven | - | Oakland Roots | 0:3 | ||||
| 2. Round | 16/04/2023 | Orange County SC | - | Indy Eleven | 1:0 | ||||
| 2. Round | 23/04/2023 | Indy Eleven | - | Monterey Bay FC | 2:3 | ||||
| 2. Round | 30/04/2023 | Indy Eleven | - | Pittsburgh Riverhounds | 1:1 | ||||
| 3. Round | 21/05/2023 | Indy Eleven | - | Colorado Springs Switchbacks | 1:0 | |
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| 4. Round | 18/06/2023 | Birmingham Legion | - | Indy Eleven | 2:1 | ||||
| 6. Round | 20/08/2023 | El Paso Locomotive | - | Indy Eleven | 2:3 | ||||
| 6. Round | 24/08/2023 | Memphis 901 | - | Indy Eleven | 0:0 | ||||
| 6. Round | 27/08/2023 | Indy Eleven | - | Loudoun United | 2:1 | ||||
| 7. Round | 03/09/2023 | Indy Eleven | - | Miami FC | 1:0 | ||||
| 7. Round | 16/09/2023 | New Mexico United | - | Indy Eleven | 3:2 | ||||
| 7. Round | 21/09/2023 | Phoenix Rising | - | Indy Eleven | 1:1 | ||||
| 7. Round | 24/09/2023 | Indy Eleven | - | Rio Grande Valley FC | 0:1 | ||||
| 7. Round | 01/10/2023 | Indy Eleven | - | Detroit City FC | 3:0 |
Colombia