[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 |
Home History
| USA MLS | 2019/09/29 21:00 | FC Cincinnati v Orlando City SC | D | 1-1 |
| USA MLS | 2019/09/22 00:30 | Houston Dynamo v Orlando City SC | L | 2-1 |
| USA MLS | 2019/09/14 23:30 | Orlando City SC v New England Revolution | D | 3-3 |
| USA MLS | 2019/09/07 23:30 | Orlando City SC v Los Angeles FC | D | 2-2 |
| USA MLS | 2019/09/01 02:30 | San Jose Earthquakes v Orlando City SC | L | 3-0 |
| USA MLS | 2019/08/24 00:00 | Orlando City SC v Atlanta United | L | 0-1 |
| USA MLS | 2019/08/18 00:00 | Minnesota United v Orlando City SC | D | 1-1 |
| USA MLS | 2019/08/14 23:30 | Orlando City SC v Sporting Kansas City | W | 1-0 |
Away History
| USA MLS | 2019/09/29 21:00 | Chicago Fire v Toronto FC | D | 2-2 |
| USA MLS | 2019/09/21 23:30 | FC Cincinnati v Chicago Fire | D | 0-0 |
| USA MLS | 2019/09/14 19:30 | Chicago Fire v FC Dallas | W | 4-0 |
| USA MLS | 2019/08/31 23:30 | Columbus Crew v Chicago Fire | D | 1-1 |
| USA MLS | 2019/08/24 23:30 | New England Revolution v Chicago Fire | L | 2-1 |
| USA MLS | 2019/08/18 00:00 | Chicago Fire v Philadelphia Union | W | 2-0 |
| USA MLS | 2019/08/15 03:00 | Portland Timbers v Chicago Fire | L | 3-2 |
| USA MLS | 2019/08/11 01:00 | Chicago Fire v CF Montreal | W | 3-2 |