| USA USL League Two | 2023/06/15 00:00 | Chicago Dutch Lions v Chicago City SC | W | 0-2 |
| USA USL League Two | 2022/06/30 00:00 | Chicago Dutch Lions v Chicago City SC | W | 3-5 |
| USA USL League Two | 2022/06/09 00:00 | Chicago City SC v Chicago Dutch Lions | W | 3-2 |
| 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 | 2023/07/21 20:00 | Chicago City SC v Cleveland Force | W | 5-1 |
| USA USL League Two | 2023/07/16 00:00 | FC Wichita v Chicago City SC | L | 2-1 |
| USA USL League Two | 2023/07/07 00:00 | Chicago City SC v FC Wichita | W | 2-0 |
| USA USL League Two | 2023/07/02 00:00 | Des Moines Menace v Chicago City SC | W | 1-2 |
| USA USL League Two | 2024/05/26 00:00 | Sueno Futures 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 | 2024/05/16 00:00 | Chicago Dutch Lions v Des Moines Menace | L | 0-5 |
| USA USL League Two | 2023/07/16 00:00 | Chicago Dutch Lions v St Charles | W | 3-1 |
| USA USL League Two | 2023/07/08 19:00 | Chicago Dutch Lions v FC Wichita | W | 4-3 |
| USA USL League Two | 2023/07/02 00:00 | Chicago Dutch Lions v Springfield ASC | L | 1-2 |
| USA USL League Two | 2023/07/01 00:30 | Peoria City v Chicago Dutch Lions | L | 5-1 |