| 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 |