1. Round | 25/03/2023 | Detroit City FC | - | Indy Eleven | 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 | 23/04/2023 | Sacramento Republic | - | Detroit City FC | 1:0 | ||||
3. Round | 14/05/2023 | Tampa Bay Rowdies | - | Detroit City FC | 5:1 | ||||
4. Round | 25/06/2023 | Detroit City FC | - | Orange County SC | 0:1 | ||||
5. Round | 13/07/2023 | Detroit City FC | - | Loudoun United | 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 | 01/10/2023 | Indy Eleven | - | Detroit City FC | 3:0 |