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