USA: USL League Two - Main |
| | River Light | Chicago City | 2:1 (1:1, 1:0) | details | 14.07.2024 |
| | Sueno | Chicago City | 2:2 (0:1, 2:1) | details | 09.07.2024 |
| | Peoria | Chicago City | 4:1 (2:1, 2:0) | details | 03.07.2024 |
| | Chicago Dutch Lions | Chicago City | 1:5 (0:3, 1:2) | details | 30.06.2024 |
| | Chicago City | Peoria | 0:2 (0:1, 0:1) | details | 27.06.2024 |
| | Chicago City | River Light | 1:3 (0:3, 1:0) | details | 19.06.2024 |
| | Chicago City | Menace | 0:2 (0:2, 0:0) | details | 13.06.2024 |
| | Chicago City | Sueno | 1:5 (1:3, 0:2) | details | 09.06.2024 |
| | Chicago City | St. Charles | 0:0 (0:0, 0:0) | details | 03.06.2024 |
| | Chicago City | Chicago Dutch Lions | 3:0 (1:0, 2:0) | details | 30.05.2024 |
| | Menace | Chicago City | 4:1 (2:1, 2:0) | details | 26.05.2024 |
| | St. Charles | Chicago City | 5:1 (3:0, 2:1) | details | 20.05.2024 |
USA: US Open Cup - Main |
| 1/128-finals | Chicago Fire II | Chicago City | 6:0 (2:0, 4:0) | details | 21.03.2024 |
USA: USL League Two - Play Offs |
| 1/8-finals | Chicago City | Flint City | 0:2 (0:2, 0:0) | details | 24.07.2023 |
| 1/16-finals | Chicago City | Cleveland Force | 5:1 (1:0, 4:1) | details | 21.07.2023 |
USA: USL League Two - Main |
| | Wichita | Chicago City | 2:1 (1:1, 1:0) | details | 16.07.2023 |
| | Chicago City | Chicago Dutch Lions | 3:0 (2:0, 1:0) | details | 14.07.2023 |
| | Chicago City | Wichita | 2:0 | details | 07.07.2023 |
| | Menace | Chicago City | 1:2 (0:0, 1:2) | details | 02.07.2023 |
| | St. Charles | Chicago City | 1:5 (0:3, 1:2) | details | 25.06.2023 |
| | Chicago City | Peoria | 2:1 (2:0, 0:1) | details | 21.06.2023 |
| | Springfield | Chicago City | 0:5 (0:4, 0:1) | details | 19.06.2023 |
| | Chicago Dutch Lions | Chicago City | 0:2 (0:0, 0:2) | details | 15.06.2023 |
| | Chicago City | St. Charles | 5:1 (2:0, 3:1) | details | 11.06.2023 |
| | Peoria | Chicago City | 0:2 | details | 04.06.2023 |
| | Chicago City | Menace | 3:1 (1:1, 2:0) | details | 29.05.2023 |
| | Chicago City | Springfield | 4:2 | details | 20.05.2023 |
USA: USL League Two - Main |
| | Springfield | Chicago City | 1:4 (1:1, 0:3) | details | 17.07.2022 |
| | Chicago City | St. Louis Lions | 3:3 (3:1, 0:2) | details | 14.07.2022 |
| | Chicago City | Chicago United | 2:4 (2:3, 0:1) | details | 07.07.2022 |
| | Chicago City | Springfield | 4:2 (2:0, 2:2) | details | 04.07.2022 |
| | Chicago United | Chicago City | 1:0 (0:0, 1:0) | details | 02.07.2022 |
| | Chicago Dutch Lions | Chicago City | 3:5 (2:1, 1:4) | details | 30.06.2022 |
| | Kaw Valley | Chicago City | 2:0 (0:0, 2:0) | details | 26.06.2022 |
| | Wichita | Chicago City | 3:1 (1:0, 2:1) | details | 25.06.2022 |
| | Chicago City | Kaw Valley | 5:3 (1:0, 4:3) | details | 19.06.2022 |
| | Chicago City | Wichita | 3:0 (1:0, 2:0) | details | 17.06.2022 |
| | Chicago City | Chicago Dutch Lions | 3:2 | details | 09.06.2022 |
| | Chicago City | Springfield | 1:0 (1:0, 0:0) | details | 02.06.2022 |
| | St. Louis Lions | Chicago City | 1:1 (0:0, 1:1) | details | 28.05.2022 |
| | Chicago United | Chicago City | 3:3 (1:1, 2:2) | details | 23.05.2022 |