| USA USL League Two | 2024/05/30 00:00 | Chicago City SC v Chicago Dutch Lions | L | 3-0 |
| USA USL League Two | 2023/06/15 00:00 | Chicago Dutch Lions v Chicago City SC | L | 0-2 |
| 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 | 2024/06/15 00:00 | Chicago Dutch Lions v Sueno | L | 1-3 |
| USA USL League Two | 2024/06/09 23:00 | Chicago Dutch Lions v St Charles | L | 1-4 |
| USA USL League Two | 2024/06/06 23:00 | St Charles v Chicago Dutch Lions | L | 8-1 |
| USA USL League Two | 2024/06/03 00:00 | Chicago Dutch Lions v River Light SC | L | 0-2 |
| USA USL League Two | 2024/05/30 00:00 | Chicago City SC v Chicago Dutch Lions | L | 3-0 |
| USA USL League Two | 2024/05/26 00:00 | Sueno v Chicago Dutch Lions | L | 3-0 |
| USA USL League Two | 2024/05/23 00:00 | Chicago Dutch Lions v Peoria City | L | 0-6 |
| USA USL League Two | 2024/05/19 00:30 | Peoria City v Chicago Dutch Lions | L | 4-0 |
| USA USL League Two | 2024/06/26 23:00 | Chicago City SC v Peoria City | L | 0-2 |
| USA USL League Two | 2024/06/19 00:00 | Chicago City SC v River Light SC | L | 1-3 |
| 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 |