Head to Head
| Jamaica - Premier League | 2023/05/07 20:15 | Montego Bay Utd v Cavalier | L | 1-2 |
| Jamaica - Premier League | 2023/02/05 20:00 | Cavalier v Montego Bay Utd | D | 0-0 |
| Jamaica - Premier League | 2022/06/01 20:00 | Montego Bay Utd v Cavalier | D | 2-2 |
| Jamaica - Premier League | 2022/02/28 20:15 | Cavalier v Montego Bay Utd | L | 3-0 |
| Jamaica - Premier League | 2019/02/24 20:00 | Montego Bay Utd v Cavalier | W | 2-1 |
| Jamaica - Premier League | 2019/01/10 22:00 | Cavalier v Montego Bay Utd | L | 2-1 |
| Jamaica - Premier League | 2018/10/21 22:00 | Cavalier v Montego Bay Utd | L | 5-1 |
| Jamaica - Premier League | 2018/02/01 22:00 | Cavalier v Montego Bay Utd | D | 0-0 |
Home History
| Jamaica - Premier League | 2023/10/31 00:30 | Waterhouse v Montego Bay Utd | L | 3-0 |
| Jamaica - Premier League | 2023/10/22 18:00 | Lime Hall v Montego Bay Utd | D | 0-0 |
| Jamaica - Premier League | 2023/05/07 20:15 | Montego Bay Utd v Cavalier | L | 1-2 |
| Jamaica - Premier League | 2023/04/30 20:00 | Tivoli Gardens v Montego Bay Utd | L | 5-2 |
| Jamaica - Premier League | 2023/04/23 22:30 | Montego Bay Utd v Harbour View FC | L | 0-1 |
| Jamaica - Premier League | 2023/04/16 20:00 | Montego Bay Utd v Faulkland FC | W | 2-1 |
| Jamaica - Premier League | 2023/04/09 18:00 | Dunbeholden FC v Montego Bay Utd | L | 4-0 |
| Jamaica - Premier League | 2023/04/04 00:30 | Montego Bay Utd v Mount Pleasant FA | D | 2-2 |
Away History
| CFU - Taça das Caraíbas | 2023/11/01 00:00 | Cavalier v Harbour View FC | D | 0-0 |
| CFU - Taça das Caraíbas | 2023/10/25 00:00 | Harbour View FC v Cavalier | W | 0-5 |
| América - Amigáveis | 2023/10/15 23:00 | Mount Pleasant FA v Cavalier | L | 3-1 |
| CFU - Taça das Caraíbas | 2023/10/05 00:06 | Golden Lion v Cavalier | W | 2-5 |
| Campeonato de Clubes da CFU | 2023/09/20 00:06 | Cavalier v Moca FC | W | 3-0 |
| Campeonato de Clubes da CFU | 2023/08/31 22:06 | Cavalier v AC Port Of Spain | W | 2-1 |
| CFU - Taça das Caraíbas | 2023/08/25 00:06 | Defence Force FC v Cavalier | D | 1-1 |
| Jamaica - Premier League | 2023/06/12 00:00 | Mount Pleasant FA v Cavalier | L | 2-1 |