Head to Head
| USA USL League Two | 2023/07/02 00:00 | Des Moines Menace v Chicago City SC | L | 1-2 |
| USA USL League Two | 2023/05/29 00:00 | Chicago City SC v Des Moines Menace | L | 3-1 |
Home History
| USA USL League Two | 2024/05/16 00:00 | Chicago Dutch Lions v Des Moines Menace | W | 0-5 |
| USA USL League Two | 2024/05/12 00:00 | Des Moines Menace v Peoria City | D | 1-1 |
| US Open Cup | 2024/04/04 00:30 | Union Omaha v Des Moines Menace | L | 3-1 |
| US Open Cup | 2024/03/21 02:30 | Capo FC v Des Moines Menace | W | 6-7 |
| USA USL League Two | 2023/07/28 23:30 | Flint City Bucks v Des Moines Menace | L | 2-0 |
| USA USL League Two | 2023/07/24 00:00 | Des Moines Menace v Thunder Bay Chill | W | 3-2 |
| USA USL League Two | 2023/07/22 00:00 | Des Moines Menace v RKC Third Coast | W | 3-1 |
| USA USL League Two | 2023/07/16 00:00 | Des Moines Menace v Peoria City | W | 3-2 |
Away History
| USA USL League Two | 2024/05/20 00:00 | St Charles v Chicago City SC | L | 5-1 |
| 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 | 2023/06/24 22:00 | St Charles v Chicago City SC | W | 1-5 |