Head to Head
| Jamaica - Premier League | 2020/01/19 20:00 | Dunbeholden FC v Cavalier | L | 1-0 |
| Jamaica - Premier League | 2020/01/05 20:00 | Dunbeholden FC v Cavalier | L | 2-0 |
| Jamaica - Premier League | 2019/09/01 22:00 | Cavalier v Dunbeholden FC | W | 3-1 |
| Jamaica - Premier League | 2019/03/03 22:00 | Cavalier v Dunbeholden FC | D | 1-1 |
| Jamaica - Premier League | 2018/12/16 22:00 | Cavalier v Dunbeholden FC | D | 1-1 |
| Jamaica - Premier League | 2018/10/28 20:00 | Dunbeholden FC v Cavalier | D | 1-1 |
Home History
| Jamaica - Premier League | 2021/07/05 20:30 | Harbour View FC v Cavalier | D | 1-1 |
| Jamaica - Premier League | 2021/06/26 20:30 | Cavalier v Humble Lions | W | 2-0 |
| Jamaica - Premier League | 2020/03/09 00:00 | Mount Pleasant FA v Cavalier | W | 0-1 |
| Jamaica - Premier League | 2020/03/03 01:00 | Cavalier v Arnett Gardens | L | 0-1 |
| Jamaica - Premier League | 2020/02/23 20:30 | UWI FC v Cavalier | W | 0-3 |
| 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 |
Away History
| Jamaica - Premier League | 2021/07/03 20:30 | Dunbeholden FC v Waterhouse | L | 0-2 |
| Jamaica - Premier League | 2021/06/27 16:00 | Portmore United v Dunbeholden FC | L | 2-0 |
| Jamaica - Premier League | 2020/03/08 22:00 | Humble Lions v Dunbeholden FC | D | 0-0 |
| Jamaica - Premier League | 2020/03/01 20:30 | Dunbeholden FC v Harbour View FC | W | 2-0 |
| Jamaica - Premier League | 2020/02/23 20:30 | Molynes United FC v Dunbeholden FC | W | 2-4 |
| Jamaica - Premier League | 2020/02/16 20:00 | Vere United v Dunbeholden FC | D | 1-1 |
| Jamaica - Premier League | 2020/01/30 20:00 | Dunbeholden FC v Portmore United | L | 1-4 |
| Jamaica - Premier League | 2020/01/25 01:00 | Waterhouse v Dunbeholden FC | L | 3-1 |
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