| USA USL League Two | 2024/05/20 00:00 | St Charles v Chicago City SC | L | 5-1 |
| USA US Open Cup | 2024/03/21 00:00 | Chicago Fire II v Chicago City SC | L | 6-0 |
| USA USL League Two | 2023/07/23 22:00 | Chicago City SC v Flint City Bucks | L | 0-2 |
| USA USL League Two | 2023/07/21 20:00 | Chicago City SC v Cleveland Force | W | 5-1 |
| 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 | 2024/05/19 00:00 | Sueno v River Light SC | W | 1-2 |