[3] Montreal Impact 0-3 Orlando City SC [10] 2019-06-01 21:00
Stadium: Saputo Stadium Round: 1
Referee: Christopher Penso Home Manager: Remi Garde Away Manager: James O'Connor
Head to Head
| USA MLS | 2019/03/16 20:00 | Orlando City SC v CF Montreal | W | 1-3 |
| USA MLS | 2018/06/23 23:50 | Orlando City SC v CF Montreal | W | 0-2 |
| USA MLS | 2018/06/13 23:30 | CF Montreal v Orlando City SC | W | 3-0 |
| USA MLS | 2017/08/05 23:30 | CF Montreal v Orlando City SC | W | 2-1 |
| USA MLS | 2017/06/17 23:30 | Orlando City SC v CF Montreal | D | 3-3 |
| USA MLS | 2016/10/02 17:00 | Orlando City SC v CF Montreal | W | 0-1 |
| USA MLS | 2016/09/07 23:30 | CF Montreal v Orlando City SC | L | 1-4 |
| USA MLS | 2016/05/21 23:30 | Orlando City SC v CF Montreal | L | 2-1 |
| USA MLS | 2015/10/03 23:30 | Orlando City SC v CF Montreal | L | 2-1 |
| USA MLS | 2015/06/21 00:00 | CF Montreal v Orlando City SC | W | 2-0 |
| USA MLS | 2015/03/28 20:00 | CF Montreal v Orlando City SC | D | 2-2 |