| VS - USL League Two | 2024/05/20 00:00 | St Charles v Chicago City SC | L | 5-1 |
| VS - USL League Two | 2023/06/24 22:00 | St Charles v Chicago City SC | W | 1-5 |
| VS - USL League Two | 2023/06/10 23:00 | Chicago City SC v St Charles | W | 5-1 |
| VS - USL League Two | 2024/05/30 00:00 | Chicago City SC v Chicago Dutch Lions | W | 3-0 |
| VS - USL League Two | 2024/05/26 00:00 | Des Moines Menace v Chicago City SC | L | 4-1 |
| VS - USL League Two | 2024/05/20 00:00 | St Charles v Chicago City SC | L | 5-1 |
| VS - US Open Cup | 2024/03/21 00:00 | Chicago Fire II v Chicago City SC | L | 6-0 |
| VS - USL League Two | 2023/07/23 22:00 | Chicago City SC v Flint City Bucks | L | 0-2 |
| VS - USL League Two | 2023/07/21 20:00 | Chicago City SC v Cleveland Force | W | 5-1 |
| VS - USL League Two | 2023/07/16 00:00 | FC Wichita v Chicago City SC | L | 2-1 |
| VS - USL League Two | 2023/07/07 00:00 | Chicago City SC v FC Wichita | W | 2-0 |
| VS - USL League Two | 2024/05/26 23:00 | River Light SC v St Charles | D | 3-3 |
| VS - USL League Two | 2024/05/20 00:00 | St Charles v Chicago City SC | W | 5-1 |
| VS - USL League Two | 2024/05/16 00:00 | Sueno Futures v St Charles | W | 1-2 |
| VS - USL League Two | 2023/07/16 00:00 | Chicago Dutch Lions v St Charles | L | 3-1 |
| VS - USL League Two | 2023/07/09 00:00 | Des Moines Menace v St Charles | L | 5-3 |
| VS - USL League Two | 2023/06/28 00:00 | St Charles v Springfield ASC | W | 1-0 |
| VS - USL League Two | 2023/06/24 22:00 | St Charles v Chicago City SC | L | 1-5 |
| VS - USL League Two | 2023/06/22 00:00 | St Charles v FC Wichita | W | 3-0 |