| 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 |
| USA USL League Two | 2023/06/18 00:00 | Des Moines Menace v Chicago Dutch Lions | L | 6-0 |
| USA USL League Two | 2023/06/15 00:00 | Chicago Dutch Lions v Chicago City SC | L | 0-2 |
| USA USL League Two | 2023/06/11 00:00 | Chicago Dutch Lions v Peoria City | W | 2-1 |
| USA USL League Two | 2023/06/04 19:00 | FC Wichita v Chicago Dutch Lions | L | 4-1 |