Stadium: Saputo Stadium
Referee: Jon Freemon Home Manager: Marco Donadel Away Manager: Gregg Berhalter
| USA MLS | 2025/03/30 00:30 | Chicago Fire v CF Montreal | D | 1-1 |
| USA MLS | 2024/09/21 23:30 | CF Montreal v Chicago Fire | W | 2-0 |
| USA MLS | 2024/03/16 18:00 | Chicago Fire v CF Montreal | L | 4-3 |
| USA MLS | 2023/09/16 23:30 | CF Montreal v Chicago Fire | D | 0-0 |
| USA MLS | 2023/07/13 00:30 | Chicago Fire v CF Montreal | L | 3-0 |
| USA MLS | 2022/09/13 23:30 | CF Montreal v Chicago Fire | W | 3-2 |
| USA MLS | 2022/08/28 00:00 | Chicago Fire v CF Montreal | W | 0-2 |
| USA MLS | 2021/09/19 17:00 | CF Montreal v Chicago Fire | W | 2-0 |
| USA MLS | 2025/05/24 23:30 | CF Montreal v Los Angeles FC | D | 2-2 |
| Canada Championships | 2025/05/20 23:00 | Forge FC v CF Montreal | L | 1-0 |
| USA MLS | 2025/05/17 18:30 | CF Montreal v Toronto FC | L | 1-6 |
| USA MLS | 2025/05/14 23:30 | CF Montreal v Columbus Crew | D | 1-1 |
| USA MLS | 2025/05/10 23:30 | New York City FC v CF Montreal | W | 0-1 |
| USA MLS | 2025/05/03 23:30 | CF Montreal v Philadelphia Union | L | 1-2 |
| Canada Championships | 2025/04/30 23:00 | Toronto FC v CF Montreal | D | 2-2 |
| USA MLS | 2025/04/26 20:30 | New York Red Bulls v CF Montreal | L | 1-0 |
| USA MLS | 2025/05/25 19:00 | New York City FC v Chicago Fire | L | 3-1 |
| USA US Open Cup | 2025/05/20 23:30 | New England Revolution v Chicago Fire | W | 1-3 |
| USA MLS | 2025/05/17 23:30 | Charlotte FC v Chicago Fire | W | 1-4 |
| USA MLS | 2025/05/10 18:30 | Chicago Fire v Atlanta United | W | 2-1 |
| USA US Open Cup | 2025/05/08 00:00 | Chicago Fire v Detroit City FC | W | 4-0 |
| USA MLS | 2025/05/04 00:30 | Chicago Fire v Orlando City SC | D | 0-0 |
| USA MLS | 2025/04/27 00:30 | Nashville SC v Chicago Fire | L | 7-2 |
| USA MLS | 2025/04/20 00:30 | Chicago Fire v FC Cincinnati | L | 2-3 |