Face à face
| Jamaïque - Premier League | 2019/02/10 20:00 | Portmore United v Cavalier | L | 1-0 |
| Jamaïque - Premier League | 2018/12/23 22:00 | Cavalier v Portmore United | W | 2-1 |
| Jamaïque - Premier League | 2018/10/07 22:00 | Cavalier v Portmore United | L | 0-2 |
| Jamaïque - Premier League | 2018/04/15 20:00 | Portmore United v Cavalier | L | 3-0 |
| Jamaïque - Premier League | 2018/04/08 23:00 | Cavalier v Portmore United | D | 0-0 |
| Jamaïque - Premier League | 2018/01/21 22:00 | Cavalier v Portmore United | W | 3-0 |
| Jamaïque - Premier League | 2017/11/28 01:35 | Cavalier v Portmore United | D | 0-0 |
| Jamaïque - Premier League | 2017/09/25 22:45 | Portmore United v Cavalier | L | 1-0 |
Home History
| Jamaïque - Premier League | 2019/10/29 01:00 | Waterhouse v Cavalier | D | 0-0 |
| Jamaïque - Premier League | 2019/10/20 20:30 | Molynes United FC v Cavalier | W | 1-3 |
| Jamaïque - Premier League | 2019/10/15 01:30 | Cavalier v Mount Pleasant FA | D | 2-2 |
| Jamaïque - Premier League | 2019/10/07 00:00 | Arnett Gardens v Cavalier | L | 2-0 |
| Jamaïque - Premier League | 2019/10/01 01:30 | Cavalier v UWI Pelicans | W | 4-0 |
| Jamaïque - Premier League | 2019/09/22 20:30 | Tivoli Gardens v Cavalier | L | 2-0 |
| Jamaïque - Premier League | 2019/09/15 22:00 | Cavalier v Humble Lions | D | 1-1 |
| Jamaïque - Premier League | 2019/09/10 01:30 | Harbour View FC v Cavalier | L | 3-0 |
Away History
| Jamaïque - Premier League | 2019/10/30 20:00 | Portmore United v Mount Pleasant FA | L | 0-2 |
| Jamaïque - Premier League | 2019/10/22 01:30 | Arnett Gardens v Portmore United | L | 1-0 |
| Jamaïque - Premier League | 2019/10/13 20:30 | Portmore United v UWI Pelicans | W | 2-1 |
| Jamaïque - Premier League | 2019/10/06 20:30 | Tivoli Gardens v Portmore United | D | 1-1 |
| Jamaïque - Premier League | 2019/09/29 20:30 | Portmore United v Humble Lions | W | 2-0 |
| Jamaïque - Premier League | 2019/09/23 00:00 | Harbour View FC v Portmore United | W | 1-2 |
| Jamaïque - Premier League | 2019/09/15 20:30 | Portmore United v Dunbeholden FC | L | 0-1 |
| Jamaïque - Premier League | 2019/09/08 20:30 | Vere United v Portmore United | L | 2-0 |
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