1. Round | 19/03/2023 | El Paso Locomotive | - | Detroit City FC | 1:3 | ||||
2. Round | 01/04/2023 | Detroit City FC | - | Rio Grande Valley FC | 0:1 | ||||
2. Round | 08/04/2023 | Louisville City FC | - | Detroit City FC | 1:0 | ||||
2. Round | 16/04/2023 | Miami FC | - | Detroit City FC | 0:0 | ||||
2. Round | 29/04/2023 | Detroit City FC | - | Tampa Bay Rowdies | 0:1 | ||||
3. Round | 07/05/2023 | Detroit City FC | - | FC Tulsa | 1:1 | ||||
4. Round | 08/06/2023 | Charleston Battery | - | Detroit City FC | 0:0 | ||||
5. Round | 16/07/2023 | Pittsburgh Riverhounds | - | Detroit City FC | 2:0 | ||||
5. Round | 30/07/2023 | Oakland Roots | - | Detroit City FC | 1:1 | ||||
6. Round | 27/08/2023 | Birmingham Legion | - | Detroit City FC | 2:3 | ||||
7. Round | 17/09/2023 | Phoenix Rising | - | Detroit City FC | 5:0 | ||||
7. Round | 24/09/2023 | Detroit City FC | - | Hartford Athletic | 3:0 |