| USA USL League Two | 2024/06/13 00:00 | Chicago City SC v Des Moines Menace | L | 0-2 |
| USA USL League Two | 2024/06/09 00:00 | Chicago City SC v Sueno | L | 1-5 |
| USA USL League Two | 2024/06/02 23:00 | Chicago City SC v St Charles | D | 0-0 |
| USA USL League Two | 2024/05/30 00:00 | Chicago City SC v Chicago Dutch Lions | W | 3-0 |
| USA USL League Two | 2024/05/26 00:00 | Des Moines Menace v Chicago City SC | L | 4-1 |
| USA USL League Two | 2024/05/20 00:00 | St Charles v Chicago City SC | L | 5-1 |
| USA US Open Cup | 2024/03/21 00:00 | Chicago Fire II v Chicago City SC | L | 6-0 |
| USA USL League Two | 2023/07/23 22:00 | Chicago City SC v Flint City Bucks | L | 0-2 |
| USA USL League Two | 2024/06/16 00:30 | Peoria City v River Light SC | L | 2-1 |
| USA USL League Two | 2024/06/13 00:00 | St Charles v River Light SC | D | 3-3 |
| USA USL League Two | 2024/06/07 00:00 | River Light SC v Peoria City | D | 2-2 |
| USA USL League Two | 2024/06/03 00:00 | Chicago Dutch Lions v River Light SC | W | 0-2 |
| USA USL League Two | 2024/05/31 00:00 | River Light SC v Des Moines Menace | W | 1-0 |
| USA USL League Two | 2024/05/26 23:00 | River Light SC v St Charles | D | 3-3 |
| USA USL League Two | 2024/05/19 00:00 | Sueno v River Light SC | W | 1-2 |