Home History
| USA USL League Two | 2023/05/20 00:30 | Chicago City SC v Springfield ASC | W | 4-2 |
| USA USL League Two | 2022/07/16 23:00 | Springfield ASC v Chicago City SC | W | 1-4 |
| USA USL League Two | 2022/07/14 00:00 | Chicago City SC v St Louis Lions | D | 3-3 |
| USA USL League Two | 2022/07/07 00:00 | Chicago City SC v Chicago FC United | L | 2-4 |
| USA USL League Two | 2022/07/03 23:00 | Chicago City SC v Springfield ASC | W | 4-2 |
| USA USL League Two | 2022/07/02 00:00 | Chicago FC United v Chicago City SC | L | 1-0 |
| USA USL League Two | 2022/06/30 00:00 | Chicago Dutch Lions v Chicago City SC | W | 3-5 |
| USA USL League Two | 2022/06/26 00:30 | Kaw Valley FC v Chicago City SC | L | 2-0 |
Away History
| USA USL League Two | 2023/05/27 00:00 | Chicago Dutch Lions v Des Moines Menace | W | 0-5 |
| USA USL League Two | 2023/05/21 00:00 | FC Wichita v Des Moines Menace | W | 1-3 |
| USA USL League Two | 2023/05/14 00:00 | Des Moines Menace v FC Wichita | W | 3-0 |
| USA USL League Two | 2023/05/08 00:00 | St Charles v Des Moines Menace | W | 0-4 |
| US Open Cup | 2023/04/06 00:00 | Des Moines Menace v Chattanooga FC | L | 1-4 |
| US Open Cup | 2023/03/23 00:00 | Beaman United FC v Des Moines Menace | W | 0-3 |
| USA USL League Two | 2022/07/30 00:15 | Des Moines Menace v Flint City Bucks | L | 5-6 |
| USA USL League Two | 2022/07/25 00:00 | Des Moines Menace v Kings Hammer FC | W | 4-1 |