[11] Chicago Fire 4-0 Orlando City SC [10] 2018-09-16 21:00
Stadium: SeatGeek Stadium Round: 1
Referee: Allen Chapman Home Manager: Veljko Paunovic Away Manager: James O'Connor
Head to Head
| 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 |
| USA US Open Cup | 2015/07/23 00:30 | Chicago Fire v Orlando City SC | W | 3-1 |
| USA MLS | 2015/06/07 00:30 | Chicago Fire v Orlando City SC | L | 2-3 |