| USA - USL League Two | 2023/07/16 00:00 | FC Wichita v Chicago City SC | L | 2-1 |
| USA - USL League Two | 2023/07/07 00:00 | Chicago City SC v FC Wichita | W | 2-0 |
| USA - USL League Two | 2023/07/02 00:00 | Des Moines Menace v Chicago City SC | W | 1-2 |
| USA - USL League Two | 2023/06/24 22:00 | St Charles v Chicago City SC | W | 1-5 |
| USA - USL League Two | 2023/06/21 00:00 | Chicago City SC v Peoria City | W | 2-1 |
| USA - USL League Two | 2023/06/19 00:00 | Springfield ASC v Chicago City SC | W | 0-5 |
| USA - USL League Two | 2023/06/15 00:00 | Chicago Dutch Lions v Chicago City SC | W | 0-2 |
| USA - USL League Two | 2023/06/10 23:00 | Chicago City SC v St Charles | W | 5-1 |
| USA - USL League Two | 2023/07/15 23:00 | Toledo Villa FC v Cleveland Force | D | 1-1 |
| USA - USL League Two | 2023/07/05 23:00 | FC Buffalo v Cleveland Force | W | 0-1 |
| USA - USL League Two | 2023/07/01 22:00 | Dayton Dutch Lions FC v Cleveland Force | W | 0-3 |
| USA - USL League Two | 2023/06/25 21:00 | Fort Wayne FC v Cleveland Force | L | 4-0 |
| USA - USL League Two | 2023/06/21 23:00 | Cleveland Force v FC Buffalo | W | 4-0 |
| USA - USL League Two | 2023/06/17 23:00 | Cleveland Force v Toledo Villa FC | W | 3-1 |
| USA - USL League Two | 2023/06/07 23:00 | Toledo Villa FC v Cleveland Force | L | 3-2 |
| USA - USL League Two | 2023/05/31 23:00 | Cleveland Force v Kings Hammer FC | D | 2-2 |