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March 9, 2025 | L | Huntsville City Football Club 4 at Chicago Fire FC II 1 | Final |
March 13, 2025 | W | Toronto FC II 0 at Chicago Fire FC II 1 | Final |
March 30, 2025 | W | Chicago Fire FC II 2 at FC Cincinnati 2 1 | Final |
April 6, 2025 | L | Chicago Fire FC II 2 at New York Red Bulls II 3 | Final |
April 20, 2025 | L | Chicago Fire FC II 0 at Huntsville City Football Club 5 | Final |
April 25, 2025 | L | Chicago Fire FC II 0 at Toronto FC II 2 | Final |
May 2, 2025 | W | Orlando City B 1 at Chicago Fire FC II 5 | Final |
May 9, 2025 | W | FC Cincinnati 2 1 at Chicago Fire FC II 2 | Final |
May 23, 2025 | T | Chicago Fire FC II 2 at New York City FC II 2 | Final (PK 2-4) |
June 1, 2025 | W | Columbus Crew 2 0 at Chicago Fire FC II 5 | Final |
June 9, 2025 | T | New England Revolution II 2 at Chicago Fire FC II 2 | Final (PK 5-4) |
June 14, 2025 | T | Chicago Fire FC II 1 at Carolina Core FC 1 | Final (PK 5-4) |
June 25, 2025 | W | Chicago Fire FC II 3 at Inter Miami CF II 1 | Final |
June 30, 2025 | T | Crown Legacy FC 1 at Chicago Fire FC II 1 | Final (PK 3-5) |
July 5, 2025 | | Chicago Fire FC II at Chattanooga FC | 7:00 p.m. |
July 13, 2025 | | New England Revolution II at Chicago Fire FC II | 2:00 p.m. |
July 20, 2025 | | Chicago Fire FC II at Toronto FC II | 3:00 p.m. |
July 27, 2025 | | New York Red Bulls II at Chicago Fire FC II | 2:00 p.m. |
August 3, 2025 | | Columbus Crew 2 at Chicago Fire FC II | 2:00 p.m. |
August 8, 2025 | | Chicago Fire FC II at New York City FC II | 7:30 p.m. |
August 15, 2025 | | Philadelphia Union II at Chicago Fire FC II | 8:00 p.m. |
August 24, 2025 | | Chicago Fire FC II at New York Red Bulls II | 7:00 p.m. |
August 31, 2025 | | Chicago Fire FC II at New England Revolution II | 3:00 p.m. |
September 10, 2025 | | FC Cincinnati 2 at Chicago Fire FC II | 8:00 p.m. |
September 14, 2025 | | New York City FC II at Chicago Fire FC II | 9:00 p.m. |
September 21, 2025 | | Chicago Fire FC II at Philadelphia Union II | 3:00 p.m. |
September 28, 2025 | | Atlanta United 2 at Chicago Fire FC II | 2:00 p.m. |
October 5, 2025 | | Chicago Fire FC II at Columbus Crew 2 | 1:00 p.m. |