| USA USL League Two | 2022/06/30 00:00 | Chicago Dutch Lions v Chicago City SC | L | 3-5 |
| USA USL League Two | 2022/06/09 00:00 | Chicago City SC v Chicago Dutch Lions | L | 3-2 |
| USA USL League Two | 2023/06/11 00:00 | Chicago Dutch Lions v Peoria City | W | 2-1 |
| USA USL League Two | 2023/06/04 19:00 | FC Wichita v Chicago Dutch Lions | L | 4-1 |
| USA USL League Two | 2023/05/31 22:00 | St Charles v Chicago Dutch Lions | L | 2-0 |
| USA USL League Two | 2023/05/27 00:00 | Chicago Dutch Lions v Des Moines Menace | L | 0-5 |
| USA USL League Two | 2023/05/24 00:00 | Springfield ASC v Chicago Dutch Lions | L | 1-0 |
| USA USL League Two | 2022/07/10 21:30 | Kaw Valley FC v Chicago Dutch Lions | L | 3-0 |
| USA USL League Two | 2022/07/06 20:00 | Chicago Dutch Lions v Springfield ASC | W | 3-1 |
| USA USL League Two | 2022/06/30 00:00 | Chicago Dutch Lions v Chicago City SC | L | 3-5 |
| USA USL League Two | 2023/06/10 23:00 | Chicago City SC v St Charles | W | 5-1 |
| USA USL League Two | 2023/06/04 00:30 | Peoria City v Chicago City SC | W | 0-2 |
| USA USL League Two | 2023/05/29 00:00 | Chicago City SC v Des Moines Menace | W | 3-1 |
| USA USL League Two | 2023/05/20 00:30 | Chicago City SC v Springfield ASC | W | 4-2 |
| USA USL League Two | 2022/07/16 23:00 | Springfield ASC v Chicago City SC | W | 1-4 |
| USA USL League Two | 2022/07/14 00:00 | Chicago City SC v St. Louis Lions | D | 3-3 |
| USA USL League Two | 2022/07/07 00:00 | Chicago City SC v Chicago FC United | L | 2-4 |
| USA USL League Two | 2022/07/03 23:00 | Chicago City SC v Springfield ASC | W | 4-2 |