Head to Head
| Jamaica - Premier League | 2019/11/24 20:00 | UWI FC v Cavalier | D | 1-1 |
| Jamaica - Premier League | 2019/10/01 01:30 | Cavalier v UWI FC | L | 4-0 |
| Jamaica - Premier League | 2019/02/05 01:35 | Cavalier v UWI FC | D | 1-1 |
| Jamaica - Premier League | 2018/12/02 20:00 | UWI FC v Cavalier | L | 0-1 |
| Jamaica - Premier League | 2018/09/30 20:30 | UWI FC v Cavalier | W | 1-0 |
| Jamaica - Premier League | 2018/03/11 20:00 | UWI FC v Cavalier | W | 2-1 |
| Jamaica - Premier League | 2017/12/21 20:00 | UWI FC v Cavalier | L | 0-1 |
| Jamaica - Premier League | 2017/11/12 20:00 | Cavalier v UWI FC | D | 1-1 |
Home History
| Jamaica - Premier League | 2020/02/17 00:00 | Mount Pleasant FA v UWI FC | L | 3-0 |
| Jamaica - Premier League | 2020/01/30 20:00 | UWI FC v Arnett Gardens | L | 1-3 |
| Jamaica - Premier League | 2020/01/26 20:00 | UWI FC v Molynes United FC | D | 1-1 |
| Jamaica - Premier League | 2020/01/19 20:00 | Tivoli Gardens v UWI FC | L | 1-0 |
| Jamaica - Premier League | 2020/01/12 20:00 | UWI FC v Dunbeholden FC | D | 0-0 |
| Jamaica - Premier League | 2020/01/06 00:00 | Waterhouse v UWI FC | D | 2-2 |
| Jamaica - Premier League | 2019/12/31 01:00 | UWI FC v Mount Pleasant FA | L | 0-3 |
| Jamaica - Premier League | 2019/12/22 20:00 | Tivoli Gardens v UWI FC | D | 2-2 |
Away History
| Jamaica - Premier League | 2020/02/18 01:00 | Cavalier v Tivoli Gardens | D | 1-1 |
| Jamaica - Premier League | 2020/01/30 22:00 | Humble Lions v Cavalier | L | 2-1 |
| Jamaica - Premier League | 2020/01/26 22:00 | Cavalier v Harbour View FC | D | 1-1 |
| Jamaica - Premier League | 2020/01/19 20:00 | Dunbeholden FC v Cavalier | L | 1-0 |
| Jamaica - Premier League | 2020/01/12 22:00 | Cavalier v Molynes United FC | W | 4-0 |
| Jamaica - Premier League | 2020/01/05 20:00 | Dunbeholden FC v Cavalier | L | 2-0 |
| Jamaica - Premier League | 2019/12/30 01:00 | Cavalier v Waterhouse | W | 1-0 |
| Jamaica - Premier League | 2019/12/23 00:00 | Mount Pleasant FA v Cavalier | W | 0-1 |