All countries
| Chicago Fire II | Chattanooga | 2:1 (1:0, 1:1) | details | 15.03.2026 | ||||
| Orlando City B | Chicago Fire II | 2:1 (1:1, 1:0) | details | 09.03.2026 | ||||
| Inter Miami II | Chicago Fire II | 1:2 AfP (0:0, 1:1, 5:6) | details | 28.02.2026 | ||||
| Indy Eleven | Chicago Fire II | 0:0 (0:0, 0:0) | details | 13.02.2026 | ||||
| Quarter-finals | New York Red Bulls II | Chicago Fire II | 5:3 AET (3:2, 0:1, 2:0) | details | 27.10.2025 | |||
| 1/8-finals | New England Revolution II | Chicago Fire II | 0:1 (0:0, 0:1) | details | 20.10.2025 | |||
| Columbus Crew 2 | Chicago Fire II | 3:4 AfP (1:2, 2:1, 2:3) | details | 05.10.2025 | ||||
| Chicago Fire II | Atlanta United 2 | 2:5 (1:3, 1:2) | details | 28.09.2025 | ||||
| Philadelphia Union II | Chicago Fire II | 5:2 (2:0, 3:2) | details | 21.09.2025 | ||||
| Chicago Fire II | New York City II | 4:5 (2:1, 2:4) | details | 15.09.2025 | ||||
| Chicago Fire II | Cincinnati 2 | 2:1 (0:0, 2:1) | details | 10.09.2025 | ||||
| New England Revolution II | Chicago Fire II | 2:3 AfP (2:1, 0:1, 1:3) | details | 31.08.2025 | ||||
| New York Red Bulls II | Chicago Fire II | 1:0 (0:0, 1:0) | details | 25.08.2025 | ||||
| Chicago Fire II | Philadelphia Union II | 2:0 (0:0, 2:0) | details | 16.08.2025 | ||||
| New York City II | Chicago Fire II | 3:4 AfP (2:2, 1:1, 1:4) | details | 09.08.2025 | ||||
| Chicago Fire II | Columbus Crew 2 | 6:1 (2:1, 4:0) | details | 03.08.2025 | ||||
| Chicago Fire II | New York Red Bulls II | 9:2 (5:1, 4:1) | details | 27.07.2025 | ||||
| Toronto FC II | Chicago Fire II | 2:3 (1:1, 1:2) | details | 20.07.2025 | ||||
| Chicago Fire II | New England Revolution II | 3:4 (2:3, 1:1) | details | 13.07.2025 | ||||
| Chattanooga | Chicago Fire II | 0:1 (0:0, 0:1) | details | 06.07.2025 | ||||
| Chicago Fire II | Crown Legacy | 2:1 AfP (0:0, 1:1, 5:3) | details | 01.07.2025 | ||||
| Inter Miami II | Chicago Fire II | 1:3 (0:1, 1:2) | details | 26.06.2025 | ||||
| Carolina Core | Chicago Fire II | 1:2 AfP (1:1, 0:0, 4:5) | details | 15.06.2025 | ||||
| Chicago Fire II | New England Revolution II | 2:3 AfP (1:1, 1:1, 4:5) | details | 09.06.2025 | ||||
| Chicago Fire II | Columbus Crew 2 | 5:0 (2:0, 3:0) | details | 01.06.2025 | ||||
| New York City II | Chicago Fire II | 3:2 AfP (1:0, 1:2, 4:2) | details | 23.05.2025 | ||||
| Chicago Fire II | Cincinnati 2 | 2:1 (1:0, 1:1) | details | 09.05.2025 | ||||
| Chicago Fire II | Orlando City B | 5:1 (2:1, 3:0) | details | 03.05.2025 | ||||
| Toronto FC II | Chicago Fire II | 2:0 (1:0, 1:0) | details | 26.04.2025 | ||||
| Huntsville | Chicago Fire II | 5:0 (4:0, 1:0) | details | 21.04.2025 | ||||
| New York Red Bulls II | Chicago Fire II | 3:2 (1:0, 2:2) | details | 06.04.2025 | ||||
| Cincinnati 2 | Chicago Fire II | 1:2 (1:1, 0:1) | details | 30.03.2025 | ||||
| Chicago Fire II | Toronto FC II | 1:0 (0:0, 1:0) | details | 14.03.2025 | ||||
| Chicago Fire II | Huntsville | 1:4 (1:3, 0:1) | details | 09.03.2025 | ||||
| Chicago Fire II | Indy Eleven | 0:3 (0:1, 0:2) | details | 15.02.2025 | ||||
| Quarter-finals | Chicago Fire II | Columbus Crew 2 | 2:3 (1:2, 1:1) | details | 27.10.2024 | |||
| 1/8-finals | Chicago Fire II | Orlando City B | 2:1 AfP (1:1, 0:0, 0:0, 5:4) | details | 20.10.2024 | |||
| Chicago Fire II | Philadelphia Union II | 2:1 (1:0, 1:1) | details | 06.10.2024 | ||||
| Columbus Crew 2 | Chicago Fire II | 0:1 (0:1, 0:0) | details | 29.09.2024 | ||||
| Orlando City B | Chicago Fire II | 3:0 (0:0, 3:0) | details | 24.09.2024 | ||||
| Chicago Fire II | New York Red Bulls II | 2:1 (2:0, 0:1) | details | 14.09.2024 | ||||
| Chicago Fire II | Cincinnati 2 | 1:2 AfP (0:0, 1:1, 3:4) | details | 08.09.2024 | ||||
| New England Revolution II | Chicago Fire II | 2:1 AfP (1:1, 0:0, 4:2) | details | 01.09.2024 | ||||
| New York City II | Chicago Fire II | 3:2 AfP (2:0, 0:2, 7:6) | details | 24.08.2024 | ||||
| Philadelphia Union II | Chicago Fire II | 3:2 (1:1, 2:1) | details | 10.08.2024 | ||||
| New York Red Bulls II | Chicago Fire II | 4:3 (2:2, 2:1) | details | 05.08.2024 | ||||
| Cincinnati 2 | Chicago Fire II | 5:0 (2:0, 3:0) | details | 29.07.2024 | ||||
| Chicago Fire II | New England Revolution II | 3:2 (3:2, 0:0) | details | 21.07.2024 | ||||
| Chicago Fire II | New York City II | 0:2 (0:1, 0:1) | details | 14.07.2024 | ||||
| Chicago Fire II | Toronto FC II | 2:0 (0:0, 2:0) | details | 10.07.2024 | ||||