Stadium: Soldier Field
Referee: Victor Rivas Home Manager: Gregg Berhalter Away Manager: Oscar Pareja
| USA MLS | 2024/06/22 23:30 | Orlando City SC v Chicago Fire | L | 4-2 |
| USA MLS | 2024/05/30 00:30 | Chicago Fire v Orlando City SC | D | 1-1 |
| USA MLS | 2023/08/21 00:30 | Chicago Fire v Orlando City SC | L | 1-3 |
| USA MLS | 2023/07/01 23:30 | Orlando City SC v Chicago Fire | L | 3-1 |
| USA MLS | 2022/04/09 17:00 | Orlando City SC v Chicago Fire | L | 1-0 |
| USA MLS | 2022/03/05 23:00 | Chicago Fire v Orlando City SC | D | 0-0 |
| USA MLS | 2021/08/22 00:00 | Orlando City SC v Chicago Fire | L | 1-0 |
| USA MLS | 2021/07/08 00:00 | Chicago Fire v Orlando City SC | W | 3-1 |
| USA MLS | 2024/10/19 22:00 | Chicago Fire v Nashville SC | L | 0-3 |
| USA MLS | 2024/10/02 23:30 | Charlotte FC v Chicago Fire | L | 4-3 |
| USA MLS | 2024/09/29 00:30 | Chicago Fire v Toronto FC | D | 1-1 |
| USA MLS | 2024/09/21 23:30 | CF Montreal v Chicago Fire | L | 2-0 |
| USA MLS | 2024/09/19 00:30 | Nashville SC v Chicago Fire | L | 1-0 |
| USA MLS | 2024/09/15 00:30 | Chicago Fire v New York Red Bulls | W | 2-1 |
| USA MLS | 2024/09/08 00:30 | Chicago Fire v DC United | L | 1-2 |
| USA MLS | 2024/09/01 00:30 | Chicago Fire v Inter Miami CF | L | 1-4 |
| USA MLS Play-Offs | 2024/12/01 00:30 | Orlando City SC v New York Red Bulls | L | 0-1 |
| USA MLS Play-Offs | 2024/11/24 20:30 | Orlando City SC v Atlanta United | W | 1-0 |
| USA MLS Play-Offs | 2024/11/09 23:00 | Orlando City SC v Charlotte FC | D | 1-1 |
| USA MLS Play-Offs | 2024/11/01 23:30 | Charlotte FC v Orlando City SC | D | 0-0 |
| USA MLS Play-Offs | 2024/10/27 23:30 | Orlando City SC v Charlotte FC | W | 2-0 |
| USA MLS | 2024/10/19 22:00 | Orlando City SC v Atlanta United | L | 1-2 |
| USA MLS | 2024/10/05 23:30 | FC Cincinnati v Orlando City SC | W | 1-3 |
| USA MLS | 2024/10/02 23:30 | Orlando City SC v Philadelphia Union | W | 2-1 |