[9] Chicago Fire 1-1 Orlando City SC [4] 2019-03-09 18:00
Stadium: SeatGeek Stadium Round: 1
Referee: Robert Sibiga Home Manager: Veljko Paunovic Away Manager: James O'Connor
Head to Head
| USA MLS | 2018/09/16 21:00 | Chicago Fire v Orlando City SC | W | 4-0 |
| USA MLS | 2018/05/26 23:30 | Orlando City SC v Chicago Fire | W | 1-2 |
| USA MLS | 2017/06/25 00:30 | Chicago Fire v Orlando City SC | W | 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 | L | 0-1 |
| USA MLS | 2015/08/29 23:30 | Orlando City SC v Chicago Fire | D | 1-1 |
Home History
| USA MLS | 2019/03/03 01:00 | LA Galaxy v Chicago Fire | L | 2-1 |
| World Club Friendlies | 2019/02/24 00:30 | Charleston Battery v Chicago Fire | W | 0-1 |
| World Club Friendlies | 2019/02/21 00:30 | FC Cincinnati v Chicago Fire | D | 1-1 |
| World Club Friendlies | 2019/02/16 22:00 | Columbus Crew v Chicago Fire | D | 1-1 |
| World Club Friendlies | 2019/02/06 10:00 | Fuenlabrada v Chicago Fire | W | 0-1 |
| Club Friendly List | 2019/01/30 15:00 | Atletico Madrid B v Chicago Fire | D | 1-1 |
| USA MLS | 2018/10/28 20:30 | Chicago Fire v DC United | D | 0-0 |
| USA MLS | 2018/10/21 19:00 | Atlanta United v Chicago Fire | L | 2-1 |
Away History
| USA MLS | 2019/03/02 19:30 | Orlando City SC v New York City FC | D | 2-2 |
| World Club Friendlies | 2019/02/21 00:30 | Orlando City SC v New England Revolution | W | 6-2 |
| World Club Friendlies | 2019/02/17 00:30 | Orlando City SC v New York City FC | W | 2-1 |
| USA MLS | 2018/10/28 20:30 | New York Red Bulls v Orlando City SC | L | 1-0 |
| USA MLS | 2018/10/21 19:00 | Orlando City SC v Columbus Crew | W | 2-1 |
| USA MLS | 2018/10/17 23:30 | Orlando City SC v Seattle Sounders | L | 1-2 |
| USA MLS | 2018/10/13 23:30 | New England Revolution v Orlando City SC | L | 2-0 |
| USA MLS | 2018/10/07 00:00 | FC Dallas v Orlando City SC | L | 2-0 |