[9] Orlando City SC 1-0 Chicago Fire [21] 2021-08-22 00:00
Stadium: Inter&Co Stadium
Referee: Tim Ford Home Manager: Oscar Pareja Away Manager: Raphael Wicky
Head to Head
| 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 | 2017/06/04 23:30 | Orlando City SC v Chicago Fire | D | 0-0 |
Home History
| USA MLS | 2021/08/19 00:30 | Nashville SC v Orlando City SC | D | 1-1 |
| Leagues Cup | 2021/08/12 23:00 | Orlando City SC v Santos Laguna | L | 0-1 |
| USA MLS | 2021/08/07 23:30 | FC Cincinnati v Orlando City SC | D | 1-1 |
| USA MLS | 2021/08/05 00:00 | Orlando City SC v Inter Miami CF | D | 1-1 |
| USA MLS | 2021/07/31 00:00 | Orlando City SC v Atlanta United | W | 3-2 |
| USA MLS | 2021/07/25 22:00 | New York City FC v Orlando City SC | L | 5-0 |
| USA MLS | 2021/07/23 00:25 | Orlando City SC v Philadelphia Union | W | 2-1 |
| USA MLS | 2021/07/17 23:30 | Toronto FC v Orlando City SC | D | 1-1 |
Away History
| USA MLS | 2021/08/18 23:30 | Inter Miami CF v Chicago Fire | L | 3-2 |
| USA MLS | 2021/08/15 22:00 | Chicago Fire v Columbus Crew | W | 1-0 |
| USA MLS | 2021/08/08 22:00 | Chicago Fire v New York Red Bulls | W | 2-1 |
| USA MLS | 2021/08/05 00:00 | Chicago Fire v New York City FC | D | 0-0 |
| USA MLS | 2021/08/01 22:00 | Philadelphia Union v Chicago Fire | D | 1-1 |
| USA MLS | 2021/07/25 00:00 | Chicago Fire v Toronto FC | L | 1-2 |
| USA MLS | 2021/07/22 00:00 | Chicago Fire v DC United | D | 2-2 |
| USA MLS | 2021/07/18 00:30 | Nashville SC v Chicago Fire | L | 5-1 |