USA US Open Cup | 03/21 00:00 | 7 | Chicago Fire II v Chicago City SC | L | 6-0 | |
USA USL League Two | 07/23 22:00 | 132 | Chicago City SC v Flint City Bucks | L | 0-2 | |
USA USL League Two | 07/21 20:00 | 5 | [1] Chicago City SC v Cleveland Force [2] | W | 5-1 | |
USA USL League Two | 07/16 00:00 | 1 | FC Wichita v Chicago City SC | L | 2-1 | |
USA USL League Two | 07/13 00:00 | 1 | [1] Chicago City SC v Chicago Dutch Lions [6] | - | Postponed | |
USA USL League Two | 07/07 00:00 | 1 | [1] Chicago City SC v FC Wichita [5] | W | 2-0 | |
USA USL League Two | 07/02 00:00 | 1 | [2] Des Moines Menace v Chicago City SC [1] | W | 1-2 | |
USA USL League Two | 06/24 22:00 | 1 | St Charles v Chicago City SC | W | 1-5 | |
USA USL League Two | 06/21 00:00 | 1 | [1] Chicago City SC v Peoria City [4] | W | 2-1 | |
USA USL League Two | 06/19 00:00 | 1 | Springfield ASC v Chicago City SC | W | 0-5 | |
USA USL League Two | 06/15 00:00 | 1 | [7] Chicago Dutch Lions v Chicago City SC [1] | W | 0-2 | |
USA USL League Two | 06/10 23:00 | 1 | [1] Chicago City SC v St Charles [3] | W | 5-1 | |
USA USL League Two | 06/04 00:30 | 1 | Peoria City v Chicago City SC | W | 0-2 | |
USA USL League Two | 05/29 00:00 | 1 | [2] Chicago City SC v Des Moines Menace [1] | W | 3-1 | |
USA USL League Two | 05/20 00:30 | 1 | [2] Chicago City SC v Springfield ASC [2] | W | 4-2 | |
USA USL League Two | 07/16 23:00 | 1 | Springfield ASC v Chicago City SC | W | 1-4 | |
USA USL League Two | 07/14 00:00 | 1 | [4] Chicago City SC v St. Louis Lions [3] | D | 3-3 | |
USA USL League Two | 07/07 00:00 | 1 | [3] Chicago City SC v Chicago FC United [1] | L | 2-4 | |
USA USL League Two | 07/03 23:00 | 1 | [4] Chicago City SC v Springfield ASC [6] | W | 4-2 | |
USA USL League Two | 07/02 00:00 | 1 | [1] Chicago FC United v Chicago City SC [4] | L | 1-0 | |
USA USL League Two | 06/30 00:00 | 1 | Chicago Dutch Lions v Chicago City SC | W | 3-5 | |
USA USL League Two | 06/26 00:30 | 1 | [3] Kaw Valley FC v Chicago City SC [4] | L | 2-0 | |
USA USL League Two | 06/25 00:00 | 1 | FC Wichita v Chicago City SC | L | 3-1 | |
USA USL League Two | 06/19 00:00 | 1 | [4] Chicago City SC v Kaw Valley FC [3] | W | 5-3 | |
USA USL League Two | 06/17 00:00 | 1 | [4] Chicago City SC v FC Wichita [7] | W | 3-0 | |
USA USL League Two | 06/09 00:00 | 1 | [3] Chicago City SC v Chicago Dutch Lions [6] | W | 3-2 | |
USA USL League Two | 06/02 00:00 | 1 | [7] Chicago City SC v Springfield ASC [4] | W | 1-0 | |
USA USL League Two | 05/28 19:00 | 1 | St. Louis Lions v Chicago City SC | D | 1-1 | |
USA USL League Two | 05/23 00:00 | 1 | Chicago FC United v Chicago City SC | D | 3-3 |