[11] Orlando City SC 2-5 Chicago Fire [8] 2019-10-06 20:00
Stadium: Inter&Co Stadium
Referee: Pierre-Luc Lauziere Home Manager: James O'Connor Away Manager: Veljko Paunovic
Head to Head
| 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 |