Head to Head
| Jamajka - Premier League | 2019/11/03 22:00 | Cavalier v Portmore United | D | 0-0 |
| Jamajka - Premier League | 2019/02/10 20:00 | Portmore United v Cavalier | W | 1-0 |
| Jamajka - Premier League | 2018/12/23 22:00 | Cavalier v Portmore United | L | 2-1 |
| Jamajka - Premier League | 2018/10/07 22:00 | Cavalier v Portmore United | W | 0-2 |
| Jamajka - Premier League | 2018/04/15 20:00 | Portmore United v Cavalier | W | 3-0 |
| Jamajka - Premier League | 2018/04/08 23:00 | Cavalier v Portmore United | D | 0-0 |
| Jamajka - Premier League | 2018/01/21 22:00 | Cavalier v Portmore United | L | 3-0 |
| Jamajka - Premier League | 2017/11/28 01:35 | Cavalier v Portmore United | D | 0-0 |
Home History
| Jamajka - Premier League | 2019/12/08 20:00 | Molynes United FC v Portmore United | W | 0-2 |
| Jamajka - Premier League | 2019/12/01 20:00 | Portmore United v Dunbeholden FC | L | 1-2 |
| Jamajka - Premier League | 2019/11/28 01:00 | Waterhouse v Portmore United | L | 4-1 |
| Jamajka - Premier League | 2019/11/24 20:00 | Portmore United v Mount Pleasant FA | W | 2-0 |
| Jamajka - Premier League | 2019/11/17 20:00 | Tivoli Gardens v Portmore United | W | 0-1 |
| Jamajka - Premier League | 2019/11/10 20:00 | Portmore United v Waterhouse | D | 1-1 |
| Jamajka - Premier League | 2019/11/03 22:00 | Cavalier v Portmore United | D | 0-0 |
| Jamajka - Premier League | 2019/10/30 20:00 | Portmore United v Mount Pleasant FA | L | 0-2 |
Away History
| Jamajka - Premier League | 2019/12/10 01:00 | Cavalier v Humble Lions | D | 1-1 |
| Jamajka - Premier League | 2019/12/02 00:00 | Harbour View FC v Cavalier | W | 1-2 |
| Jamajka - Premier League | 2019/11/27 22:00 | Cavalier v Vere United | W | 6-1 |
| Jamajka - Premier League | 2019/11/24 20:00 | UWI FC v Cavalier | D | 1-1 |
| Jamajka - Premier League | 2019/11/18 01:00 | Cavalier v Arnett Gardens | L | 2-4 |
| Jamajka - Premier League | 2019/11/10 20:00 | Vere United v Cavalier | D | 0-0 |
| Jamajka - Premier League | 2019/11/03 22:00 | Cavalier v Portmore United | D | 0-0 |
| Jamajka - Premier League | 2019/10/29 01:00 | Waterhouse v Cavalier | D | 0-0 |
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