[7] Orlando City SC 4-1 Chicago Fire [24] 2020-09-19 23:30
Stadium: Inter&Co Stadium
Referee: Nima Saghafi Home Manager: Oscar Pareja Away Manager: Raphael Wicky
Head to Head
| 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 |
| USA MLS | 2016/08/14 20:00 | Chicago Fire v Orlando City SC | D | 2-2 |
| USA MLS | 2016/03/12 00:00 | Orlando City SC v Chicago Fire | D | 1-1 |
| USA MLS | 2015/09/20 00:30 | Chicago Fire v Orlando City SC | W | 0-1 |
| USA MLS | 2015/08/29 23:30 | Orlando City SC v Chicago Fire | D | 1-1 |
| USA US Open Cup | 2015/07/23 00:30 | Chicago Fire v Orlando City SC | L | 3-1 |
| USA MLS | 2015/06/07 00:30 | Chicago Fire v Orlando City SC | W | 2-3 |