Head to Head
| Jamaica Premier League | 2023/12/31 22:15 | Cavalier v Dunbeholden FC | L | 1-0 |
| Jamaica Cup | 2023/05/19 22:00 | Dunbeholden FC v Cavalier | L | 0-3 |
| Jamaica Cup | 2023/05/13 01:00 | Cavalier v Dunbeholden FC | L | 1-0 |
| Jamaica Premier League | 2023/03/12 20:00 | Cavalier v Dunbeholden FC | L | 3-1 |
| Jamaica Premier League | 2022/11/20 22:30 | Dunbeholden FC v Cavalier | L | 1-2 |
| Jamaica Premier League | 2022/06/30 00:30 | Dunbeholden FC v Cavalier | W | 7-6 |
| Jamaica Premier League | 2022/06/26 20:00 | Cavalier v Dunbeholden FC | W | 0-1 |
| Jamaica Premier League | 2022/06/09 22:00 | Dunbeholden FC v Cavalier | D | 1-1 |
Home History
| Jamaica Premier League | 2024/03/24 21:00 | Waterhouse v Dunbeholden FC | L | 1-0 |
| Jamaica Premier League | 2024/03/20 20:30 | Dunbeholden FC v Montego Bay Utd | L | 0-2 |
| Jamaica Premier League | 2024/03/10 20:30 | Tivoli Gardens v Dunbeholden FC | D | 1-1 |
| Jamaica Premier League | 2024/03/05 00:30 | Dunbeholden FC v Harbour View FC | W | 3-0 |
| Jamaica Premier League | 2024/02/25 18:00 | Molynes United FC v Dunbeholden FC | W | 2-4 |
| Jamaica Premier League | 2024/02/18 18:00 | Lime Hall v Dunbeholden FC | W | 1-4 |
| Jamaica Premier League | 2024/02/11 20:30 | Dunbeholden FC v Treasure Beach FC | D | 1-1 |
| Jamaica Premier League | 2024/02/04 20:00 | Portmore United v Dunbeholden FC | D | 1-1 |
Away History
| Jamaica Premier League | 2024/03/24 20:30 | Treasure Beach FC v Cavalier | W | 0-5 |
| Jamaica Premier League | 2024/03/18 22:00 | Cavalier v Portmore United | L | 0-1 |
| Jamaica Premier League | 2024/03/10 20:30 | Mount Pleasant FA v Cavalier | L | 2-0 |
| Jamaica Premier League | 2024/03/08 00:00 | Arnett Gardens v Cavalier | D | 2-2 |
| Jamaica Premier League | 2024/03/04 22:00 | Cavalier v Humble Lions | D | 1-1 |
| CONCACAF Champions Cup | 2024/02/29 00:00 | FC Cincinnati v Cavalier | L | 4-0 |
| CONCACAF Champions Cup | 2024/02/23 02:00 | Cavalier v FC Cincinnati | L | 0-2 |
| Jamaica Premier League | 2024/02/18 21:00 | Cavalier v Vere United | W | 2-0 |
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