| 14/07/2024 |   River Light vs Chicago City | 2 - 1 | USL League Two
Phase : J17 | 2024 | Spartan Athletic Park |
| 09/07/2024 |  Sueno vs Chicago City | 2 - 2 | USL League Two
Phase : J15 | 2024 | Stade Joliet Memorial |
| 03/07/2024 |  Peoria vs Chicago City | 4 - 1 | USL League Two
Phase : J14 | 2024 | Stade Shea |
| 30/06/2024 |  Chicago Dutch Lions vs Chicago City | 1 - 5 | USL League Two
Phase : J13 | 2024 | Spartan Athletic Park |
| 27/06/2024 | Chicago City vs Peoria | 0 - 2 | USL League Two
Phase : J12 | 2024 | Hoyne Field |
| 19/06/2024 | Chicago City vs River Light | 1 - 3 | USL League Two
Phase : J10 | 2024 | Hoyne Field |
| 13/06/2024 |  Chicago City vs Des Moines Menace | 0 - 2 | USL League Two
Phase : J8 | 2024 | Hoyne Field |
| 09/06/2024 | Chicago City vs Sueno | 1 - 5 | USL League Two
Phase : J8 | 2024 | Hoyne Field |
| 03/06/2024 |  Chicago City vs St. Charles | 0 - 0 | USL League Two
Phase : J6 | 2024 | Hoyne Field |
| 30/05/2024 | Chicago City vs Chicago Dutch Lions | 0 - 3 | USL League Two
Phase : J4 | 2024 | Hoyne Field |
| 26/05/2024 | Des Moines Menace vs Chicago City | 4 - 1 | USL League Two
Phase : J4 | 2024 | Stade Drake |
| 20/05/2024 | St. Charles vs Chicago City | 5 - 1 | USL League Two
Phase : J2 | 2024 | Lutheran High School St. Charles Foot Ball Field |
| 21/03/2024 |  Chicago Fire II vs Chicago City | 6 - 0 | US Open Cup
Phase : Tour 1 | 2024 | Stade SeatGeek |
| 23/07/2023 |  Chicago City vs Flint City Bucks | 0 - 2 | USL League Two
Phase : Conference - Semi-finals | 2023 | Stade Bishop John D’Arcy |
| 21/07/2023 |  Chicago City vs Cleveland Force | 5 - 1 | USL League Two
Phase : Conference - Quarter-finals | 2023 | Stade Bishop John D’Arcy |
| 16/07/2023 |  Wichita vs Chicago City | 2 - 1 | USL League Two
Phase : J17 | 2023 | Stryker Soccer Complex |
| 14/07/2023 | Chicago City vs Chicago Dutch Lions | 3 - 0 | USL League Two
Phase : J16 | 2023 | Spartan Athletic Park |
| 07/07/2023 | Chicago City vs Wichita | 2 - 0 | USL League Two
Phase : J14 | 2023 | Complexe sportif Lions for Hope |
| 02/07/2023 | Des Moines Menace vs Chicago City | 1 - 2 | USL League Two
Phase : J13 | 2023 | Stade Valley |
| 24/06/2023 | St. Charles vs Chicago City | 1 - 5 | USL League Two
Phase : J11 | 2023 | Lutheran High School St. Charles Foot Ball Field |
| 21/06/2023 | Chicago City vs Peoria | 2 - 1 | USL League Two
Phase : J10 | 2023 | Complexe sportif Lions for Hope |
| 19/06/2023 |  Springfield ASC vs Chicago City | 0 - 5 | USL League Two
Phase : J10 | 2023 | Sacred Heart-Griffin High School |
| 15/06/2023 | Chicago Dutch Lions vs Chicago City | 0 - 2 | USL League Two
Phase : J9 | 2023 | Spartan Athletic Park |
| 11/06/2023 | Chicago City vs St. Charles | 5 - 1 | USL League Two
Phase : J8 | 2023 | Complexe sportif Lions for Hope |
| 04/06/2023 | Peoria vs Chicago City | 0 - 2 | USL League Two
Phase : J6 | 2023 | Stade Shea |
| 29/05/2023 | Chicago City vs Des Moines Menace | 3 - 1 | USL League Two
Phase : J5 | 2023 | Complexe sportif Lions for Hope |
| 20/05/2023 | Chicago City vs Springfield ASC | 4 - 2 | USL League Two
Phase : J2 | 2023 | Complexe sportif Lions for Hope |
| 17/07/2022 | Springfield ASC vs Chicago City | 2 - 4 | USL League Two
Phase : J74 | 2022 | Sacred Heart-Griffin High School |
| 14/07/2022 |  Chicago City vs Saint Louis | 3 - 3 | USL League Two
Phase : J71 | 2022 | ITW Speer Academy |
| 07/07/2022 | Chicago City vs Chicago Fire II | 2 - 4 | USL League Two
Phase : J62 | 2022 | ITW Speer Academy |
| 04/07/2022 | Chicago City vs Springfield ASC | 4 - 2 | USL League Two
Phase : J59 | 2022 | Complexe sportif Lions for Hope |
| 02/07/2022 | Chicago Fire II vs Chicago City | 1 - 0 | USL League Two
Phase : J56 | 2022 | Stade SeatGeek |
| 30/06/2022 | Chicago Dutch Lions vs Chicago City | 3 - 5 | USL League Two
Phase : J54 | 2022 | Stade Joe Bean |
| 26/06/2022 |  Kaw Valley vs Chicago City | 2 - 0 | USL League Two
Phase : J50 | 2022 | Mercy Victory Field |
| 25/06/2022 | Wichita vs Chicago City | 3 - 1 | USL League Two
Phase : J48 | 2022 | Stryker Soccer Complex |
| 19/06/2022 | Chicago City vs Kaw Valley | 5 - 3 | USL League Two
Phase : J41 | 2022 | Complexe sportif Lions for Hope |
| 17/06/2022 | Chicago City vs Wichita | 3 - 0 | USL League Two
Phase : J37 | 2022 | ITW Speer Academy |
| 09/06/2022 | Chicago City vs Chicago Dutch Lions | 3 - 2 | USL League Two
Phase : J29 | 2022 | ITW Speer Academy |
| 02/06/2022 | Chicago City vs Springfield ASC | 1 - 0 | USL League Two
Phase : J21 | 2022 | Stade Cacciatore |
| 28/05/2022 | Saint Louis vs Chicago City | 1 - 1 | USL League Two
Phase : J16 | 2022 | Tony Glavin Soccer Complex |
| 23/05/2022 | Chicago Fire II vs Chicago City | 3 - 3 | USL League Two
Phase : J11 | 2022 | Stade SeatGeek |
