| USA USL League Two | 2023/06/04 00:30 | Peoria City v Chicago City SC | W | 0-2 |
| USA USL League Two | 2023/05/29 00:00 | Chicago City SC v Des Moines Menace | W | 3-1 |
| USA USL League Two | 2023/05/20 00:30 | Chicago City SC v Springfield ASC | W | 4-2 |
| USA USL League Two | 2022/07/16 23:00 | Springfield ASC v Chicago City SC | W | 1-4 |
| USA USL League Two | 2022/07/14 00:00 | Chicago City SC v St. Louis Lions | D | 3-3 |
| USA USL League Two | 2022/07/07 00:00 | Chicago City SC v Chicago FC United | L | 2-4 |
| USA USL League Two | 2022/07/03 23:00 | Chicago City SC v Springfield ASC | W | 4-2 |
| USA USL League Two | 2022/07/02 00:00 | Chicago FC United v Chicago City SC | L | 1-0 |
| USA USL League Two | 2023/06/05 00:00 | Springfield ASC v St Charles | W | 1-3 |
| USA USL League Two | 2023/05/31 22:00 | St Charles v Chicago Dutch Lions | W | 2-0 |
| USA USL League Two | 2023/05/21 00:30 | Peoria City v St Charles | W | 2-3 |
| USA USL League Two | 2023/05/08 00:00 | St Charles v Des Moines Menace | L | 0-4 |