| USL, League Two, Playoffs | 2022/07/16 23:00 | Springfield Asc v Chicago City SC | W | 1-4 |
| USL, League Two, Playoffs | 2022/07/03 23:00 | Chicago City SC v Springfield Asc | W | 4-2 |
| USL, League Two, Playoffs | 2022/06/02 00:00 | Chicago City SC v Springfield Asc | W | 1-0 |
| USL, League Two, Playoffs | 2022/07/16 23:00 | Springfield Asc v Chicago City SC | W | 1-4 |
| USL, League Two, Playoffs | 2022/07/14 00:00 | Chicago City SC v ST. 루이스라이온스 | D | 3-3 |
| USL, League Two, Playoffs | 2022/07/07 00:00 | Chicago City SC v 시카고 FC 유나이티드 | L | 2-4 |
| USL, League Two, Playoffs | 2022/07/03 23:00 | Chicago City SC v Springfield Asc | W | 4-2 |
| USL, League Two, Playoffs | 2022/07/02 00:00 | 시카고 FC 유나이티드 v Chicago City SC | L | 1-0 |
| USL, League Two, Playoffs | 2022/06/30 00:00 | Chicago Dutch Lions FC v Chicago City SC | W | 3-5 |
| USL, League Two, Playoffs | 2022/06/26 00:30 | 코 밸리 FC v Chicago City SC | L | 2-0 |
| USL, League Two, Playoffs | 2022/06/25 00:00 | FC 위치타 v Chicago City SC | L | 3-1 |
| USL, League Two, Playoffs | 2022/07/16 23:00 | Springfield Asc v Chicago City SC | L | 1-4 |
| USL, League Two, Playoffs | 2022/07/10 00:00 | 시카고 FC 유나이티드 v Springfield Asc | L | 3-1 |
| USL, League Two, Playoffs | 2022/07/06 20:00 | Chicago Dutch Lions FC v Springfield Asc | L | 3-1 |
| USL, League Two, Playoffs | 2022/07/03 23:00 | Chicago City SC v Springfield Asc | L | 4-2 |
| USL, League Two, Playoffs | 2022/06/23 00:00 | Springfield Asc v ST. 루이스라이온스 | L | 1-4 |
| USL, League Two, Playoffs | 2022/06/18 22:00 | ST. 루이스라이온스 v Springfield Asc | L | 4-1 |
| USL, League Two, Playoffs | 2022/06/12 22:30 | 코 밸리 FC v Springfield Asc | L | 4-1 |
| USL, League Two, Playoffs | 2022/06/09 00:00 | Springfield Asc v 시카고 FC 유나이티드 | L | 1-7 |