Stadium: Inter&Co Stadium
Referee: Victor Rivas Home Manager: Oscar Pareja Away Manager: Ezra Hendrickson
| USA MLS | 2021/08/22 00:00 | Orlando City SC v Chicago Fire | W | 1-0 |
| USA MLS | 2021/07/08 00:00 | Chicago Fire v Orlando City SC | L | 3-1 |
| USA MLS | 2020/09/19 23:30 | Orlando City SC v Chicago Fire | W | 4-1 |
| USA MLS | 2019/10/06 20:00 | Orlando City SC v Chicago Fire | L | 2-5 |
| USA MLS | 2019/03/09 18:00 | Chicago Fire v Orlando City SC | D | 1-1 |
| USA MLS | 2018/09/16 21:00 | Chicago Fire v Orlando City SC | L | 4-0 |
| USA MLS | 2018/05/26 23:30 | Orlando City SC v Chicago Fire | L | 1-2 |
| USA MLS | 2017/06/25 00:30 | Chicago Fire v Orlando City SC | L | 4-0 |
| USA MLS | 2021/11/24 01:00 | Nashville SC v Orlando City SC | L | 3-1 |
| USA MLS | 2021/11/07 20:30 | CF Montreal v Orlando City SC | W | 0-2 |
| USA MLS | 2021/10/31 20:00 | Orlando City SC v Nashville SC | D | 1-1 |
| USA MLS | 2021/10/27 23:30 | Columbus Crew v Orlando City SC | L | 3-2 |
| USA MLS | 2021/10/24 23:30 | Orlando City SC v New England Revolution | D | 2-2 |
| USA MLS | 2021/10/20 23:30 | Orlando City SC v CF Montreal | D | 1-1 |
| USA MLS | 2021/10/16 23:30 | FC Cincinnati v Orlando City SC | W | 0-1 |
| USA MLS | 2021/10/02 23:30 | Orlando City SC v DC United | W | 2-1 |
| USA MLS | 2021/11/07 20:30 | Columbus Crew v Chicago Fire | L | 2-0 |
| USA MLS | 2021/10/27 23:30 | New York City FC v Chicago Fire | L | 1-0 |
| USA MLS | 2021/10/24 00:00 | Chicago Fire v Real Salt Lake | W | 1-0 |
| USA MLS | 2021/10/20 23:30 | FC Cincinnati v Chicago Fire | W | 3-4 |
| USA MLS | 2021/10/16 23:00 | New England Revolution v Chicago Fire | D | 2-2 |
| USA MLS | 2021/10/03 20:00 | Toronto FC v Chicago Fire | L | 3-1 |
| USA MLS | 2021/09/30 00:00 | Chicago Fire v New York City FC | W | 2-0 |
| USA MLS | 2021/09/26 17:00 | Chicago Fire v Nashville SC | D | 0-0 |