| USA USL League Two | 2022/06/02 00:00 | Chicago City SC v Springfield ASC | W | 1-0 |
| USA USL League Two | 2022/05/28 19:00 | St Louis Lions v Chicago City SC | D | 1-1 |
| USA USL League Two | 2022/05/23 00:00 | Chicago FC United v Chicago City SC | D | 3-3 |
| USA USL League Two | 2022/06/04 22:00 | St Louis Lions v Chicago Dutch Lions | L | 7-2 |
| USA USL League Two | 2022/05/26 23:00 | Chicago Dutch Lions v Chicago FC United | L | 1-4 |
| USA USL League Two | 2022/05/25 00:00 | Springfield ASC v Chicago Dutch Lions | W | 1-2 |