Head to Head
| Jamaica Premier League | 2019/09/01 22:00 | Cavalier v Dunbeholden FC | L | 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 | 2019/12/29 20:00 | Molynes United FC v Dunbeholden FC | W | 2-3 |
| Jamaica Premier League | 2019/12/23 01:00 | Arnett Gardens v Dunbeholden FC | W | 0-3 |
| Jamaica Premier League | 2019/12/15 20:00 | Dunbeholden FC v Waterhouse | D | 1-1 |
| Jamaica Premier League | 2019/12/13 00:00 | Mount Pleasant FA v Dunbeholden FC | L | 2-1 |
| Jamaica Premier League | 2019/12/08 20:00 | Dunbeholden FC v Tivoli Gardens | L | 0-1 |
| Jamaica Premier League | 2019/12/01 20:00 | Portmore United v Dunbeholden FC | W | 1-2 |
| Jamaica Premier League | 2019/11/27 20:00 | Dunbeholden FC v Humble Lions | D | 1-1 |
| Jamaica Premier League | 2019/11/25 00:00 | Harbour View FC v Dunbeholden FC | W | 1-2 |
Away History
| 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 |
| Jamaica Premier League | 2019/12/17 01:00 | Cavalier v Tivoli Gardens | L | 2-3 |
| Jamaica Premier League | 2019/12/12 20:00 | Portmore United v Cavalier | L | 2-1 |
| Jamaica Premier League | 2019/12/10 01:00 | Cavalier v Humble Lions | D | 1-1 |
| Jamaica Premier League | 2019/12/02 00:00 | Harbour View FC v Cavalier | W | 1-2 |
| Jamaica Premier League | 2019/11/27 22:00 | Cavalier v Vere United | W | 6-1 |
| Jamaica Premier League | 2019/11/24 20:00 | UWI FC v Cavalier | D | 1-1 |