| 4. Round | 08/06/2023 | Charleston Battery | - | Detroit City FC | 0:0 | ||||
| 4. Round | 15/06/2023 | Hartford Athletic | - | Detroit City FC | 1:3 | ||||
| 4. Round | 18/06/2023 | Memphis 901 | - | Detroit City FC | 0:0 | ||||
| 4. Round | 25/06/2023 | Detroit City FC | - | Orange County SC | 0:1 | ||||
| 5. Round | 01/07/2023 | FC Tulsa | - | Detroit City FC | 3:2 | ||||
| 5. Round | 09/07/2023 | New Mexico United | - | Detroit City FC | 1:0 | ||||
| 5. Round | 13/07/2023 | Detroit City FC | - | Loudoun United | 1:1 |  |
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| 5. Round | 16/07/2023 | Pittsburgh Riverhounds | - | Detroit City FC | 2:0 | ||||
| 5. Round | 20/07/2023 | Detroit City FC | - | Louisville City FC | 2:0 | ||||
| 5. Round | 23/07/2023 | Detroit City FC | - | Monterey Bay FC | 1:0 | ||||
| 5. Round | 30/07/2023 | Oakland Roots | - | Detroit City FC | 1:1 | ||||
| 6. Round | 13/08/2023 | Detroit City FC | - | Charleston Battery | 0:1 | ||||
| 7. Round | 10/09/2023 | Detroit City FC | - | Miami FC | 2:1 | ||||
| 7. Round | 17/09/2023 | Phoenix Rising | - | Detroit City FC | 5:0 | ||||
| 7. Round | 24/09/2023 | Detroit City FC | - | Hartford Athletic | 3:0 | |
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| 7. Round | 28/09/2023 | Detroit City FC | - | Colorado Springs Switchbacks | 0:3 | ||||
| 7. Round | 01/10/2023 | Indy Eleven | - | Detroit City FC | 3:0 |
Cuba