| USL, League Two, Playoffs | 2024/05/20 00:00 | St Charles v Chicago City SC | L | 5-1 |
| USL, League Two, Playoffs | 2023/06/24 22:00 | St Charles v Chicago City SC | W | 1-5 |
| USL, League Two, Playoffs | 2023/06/10 23:00 | Chicago City SC v St Charles | W | 5-1 |
| USL, League Two, Playoffs | 2024/05/20 00:00 | St Charles v Chicago City SC | L | 5-1 |
| 미국 오픈 컵 | 2024/03/21 00:00 | Chicago Fire FC II v Chicago City SC | L | 6-0 |
| USL, League Two, Playoffs | 2023/07/23 22:00 | Chicago City SC v 플린트 시티 벅스 | L | 0-2 |
| USL, League Two, Playoffs | 2023/07/21 20:00 | Chicago City SC v Cleveland Force SC | W | 5-1 |
| USL, League Two, Playoffs | 2023/07/16 00:00 | FC 위치타 v Chicago City SC | L | 2-1 |
| USL, League Two, Playoffs | 2023/07/07 00:00 | Chicago City SC v FC 위치타 | W | 2-0 |
| USL, League Two, Playoffs | 2023/07/02 00:00 | 데스 모인즈 메나스 v Chicago City SC | W | 1-2 |
| USL, League Two, Playoffs | 2023/06/24 22:00 | St Charles v Chicago City SC | W | 1-5 |
| USL, League Two, Playoffs | 2024/05/20 00:00 | St Charles v Chicago City SC | W | 5-1 |
| USL, League Two, Playoffs | 2024/05/16 00:00 | Sueno FC v St Charles | W | 1-2 |
| USL, League Two, Playoffs | 2023/07/16 00:00 | Chicago Dutch Lions FC v St Charles | L | 3-1 |
| USL, League Two, Playoffs | 2023/07/09 00:00 | 데스 모인즈 메나스 v St Charles | L | 5-3 |
| USL, League Two, Playoffs | 2023/06/28 00:00 | St Charles v Springfield Asc | W | 1-0 |
| USL, League Two, Playoffs | 2023/06/24 22:00 | St Charles v Chicago City SC | L | 1-5 |
| USL, League Two, Playoffs | 2023/06/22 00:00 | St Charles v FC 위치타 | W | 3-0 |
| USL, League Two, Playoffs | 2023/06/18 00:00 | FC 위치타 v St Charles | W | 3-4 |