| USL, League Two, Playoffs | 2024/05/30 00:00 | Chicago City SC v Chicago Dutch Lions FC | L | 3-0 |
| USL, League Two, Playoffs | 2023/06/15 00:00 | Chicago Dutch Lions FC v Chicago City SC | L | 0-2 |
| USL, League Two, Playoffs | 2022/06/30 00:00 | Chicago Dutch Lions FC v Chicago City SC | L | 3-5 |
| USL, League Two, Playoffs | 2022/06/09 00:00 | Chicago City SC v Chicago Dutch Lions FC | L | 3-2 |
| USL, League Two, Playoffs | 2024/06/06 23:00 | St Charles v Chicago Dutch Lions FC | L | 8-1 |
| USL, League Two, Playoffs | 2024/06/03 00:00 | Chicago Dutch Lions FC v River Light SC | L | 0-2 |
| USL, League Two, Playoffs | 2024/05/30 00:00 | Chicago City SC v Chicago Dutch Lions FC | L | 3-0 |
| USL, League Two, Playoffs | 2024/05/26 00:00 | Sueno Futures v Chicago Dutch Lions FC | L | 3-0 |
| USL, League Two, Playoffs | 2024/05/23 00:00 | Chicago Dutch Lions FC v Peoria City | L | 0-6 |
| USL, League Two, Playoffs | 2024/05/19 00:30 | Peoria City v Chicago Dutch Lions FC | L | 4-0 |
| USL, League Two, Playoffs | 2024/05/16 00:00 | Chicago Dutch Lions FC v 데스 모인즈 메나스 | L | 0-5 |
| USL, League Two, Playoffs | 2023/07/16 00:00 | Chicago Dutch Lions FC v St Charles | W | 3-1 |
| USL, League Two, Playoffs | 2024/06/02 23:00 | Chicago City SC v St Charles | D | 0-0 |
| USL, League Two, Playoffs | 2024/05/30 00:00 | Chicago City SC v Chicago Dutch Lions FC | W | 3-0 |
| USL, League Two, Playoffs | 2024/05/26 00:00 | 데스 모인즈 메나스 v Chicago City SC | L | 4-1 |
| 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 |