[14] Chicago Fire 1-1 Orlando City SC [10] 2024-05-30 00:30
Stadium: Soldier Field
Referee: Malik Badawi Home Manager: Frank Klopas Away Manager: Oscar Pareja
Head to Head
| VS - MLS | 2023/08/21 00:30 | Chicago Fire v Orlando City SC | L | 1-3 |
| VS - MLS | 2023/07/01 23:30 | Orlando City SC v Chicago Fire | L | 3-1 |
| VS - MLS | 2022/04/09 17:00 | Orlando City SC v Chicago Fire | L | 1-0 |
| VS - MLS | 2022/03/05 23:00 | Chicago Fire v Orlando City SC | D | 0-0 |
| VS - MLS | 2021/08/22 00:00 | Orlando City SC v Chicago Fire | L | 1-0 |
| VS - MLS | 2021/07/08 00:00 | Chicago Fire v Orlando City SC | W | 3-1 |
| VS - MLS | 2020/09/19 23:30 | Orlando City SC v Chicago Fire | L | 4-1 |
| VS - MLS | 2019/10/06 20:00 | Orlando City SC v Chicago Fire | W | 2-5 |
| VS - MLS | 2019/03/09 18:00 | Chicago Fire v Orlando City SC | D | 1-1 |
| VS - MLS | 2018/09/16 21:00 | Chicago Fire v Orlando City SC | W | 4-0 |
| VS - MLS | 2018/05/26 23:30 | Orlando City SC v Chicago Fire | W | 1-2 |
| VS - MLS | 2017/06/25 00:30 | Chicago Fire v Orlando City SC | W | 4-0 |
| VS - MLS | 2017/06/04 23:30 | Orlando City SC v Chicago Fire | D | 0-0 |
| VS - MLS | 2016/08/14 20:00 | Chicago Fire v Orlando City SC | D | 2-2 |
| VS - MLS | 2016/03/12 00:00 | Orlando City SC v Chicago Fire | D | 1-1 |
| VS - MLS | 2015/09/20 00:30 | Chicago Fire v Orlando City SC | L | 0-1 |
| VS - MLS | 2015/08/29 23:30 | Orlando City SC v Chicago Fire | D | 1-1 |
| VS - US Open Cup | 2015/07/23 00:30 | Chicago Fire v Orlando City SC | W | 3-1 |
| VS - MLS | 2015/06/07 00:30 | Chicago Fire v Orlando City SC | L | 2-3 |