Head to Head
| USA - MLS | 2024/04/20 23:30 | CF Montreal v Orlando City SC | D | 2-2 |
| USA - MLS | 2024/02/25 00:30 | Orlando City SC v CF Montreal | D | 0-0 |
| USA - MLS | 2023/09/30 23:30 | Orlando City SC v CF Montreal | W | 3-0 |
| USA - MLS | 2023/05/06 23:30 | CF Montreal v Orlando City SC | L | 2-0 |
| USA - MLS - Play-Offs | 2022/10/17 00:00 | CF Montreal v Orlando City SC | L | 2-0 |
| USA - MLS | 2022/05/07 20:00 | CF Montreal v Orlando City SC | L | 4-1 |
| USA - MLS | 2022/02/27 18:00 | Orlando City SC v CF Montreal | W | 2-0 |
| USA - MLS | 2021/11/07 20:30 | CF Montreal v Orlando City SC | W | 0-2 |
| USA - MLS | 2021/10/20 23:30 | Orlando City SC v CF Montreal | D | 1-1 |
| USA - MLS | 2021/09/15 23:30 | Orlando City SC v CF Montreal | L | 2-4 |
| USA - MLS | 2020/11/02 00:30 | CF Montreal v Orlando City SC | W | 0-1 |
| USA - MLS is Back Tournament | 2020/07/26 00:00 | Orlando City SC v CF Montreal | W | 1-0 |
| Freundschaftsspiele - Vereinsmannschaften weltweit | 2020/02/08 23:00 | Orlando City SC v CF Montreal | W | 1-0 |
| USA - MLS | 2019/06/01 21:00 | CF Montreal v Orlando City SC | W | 0-3 |
| USA - MLS | 2019/03/16 20:00 | Orlando City SC v CF Montreal | L | 1-3 |
| 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 |