| 2. Round | 17/03/2024 | Colorado Springs Switchbacks | - | Detroit City FC | 1:2 | ||||
| 3. Round | 23/03/2024 | Detroit City FC | - | Loudoun United | 2:1 | ||||
| 4. Round | 30/03/2024 | Indy Eleven | - | Detroit City FC | 1:2 |  |
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| 5. Round | 06/04/2024 | Detroit City FC | - | North Carolina FC | 1:0 | ||||
| 8. Round | 28/04/2024 | Pittsburgh Riverhounds | - | Detroit City FC | 2:0 | ||||
| 9. Round | 05/05/2024 | Loudoun United | - | Detroit City FC | 0:0 | ||||
| 10. Round | 11/05/2024 | Detroit City FC | - | Phoenix Rising | 1:1 | ||||
| 13. Round | 30/05/2024 | Louisville City FC | - | Detroit City FC | 5:1 | ||||
| 13. Round | 02/06/2024 | Orange County SC | - | Detroit City FC | 3:2 |
England
