Head to Head
| Jamaica - Premier League | 2022/04/17 20:00 | Portmore United v Cavalier | D | 0-0 |
| Jamaica - Premier League | 2022/01/30 20:15 | Cavalier v Portmore United | W | 0-1 |
| Jamaica - Premier League | 2021/09/03 18:00 | Cavalier v Portmore United | L | 1-0 |
| Jamaica - Premier League | 2019/12/12 20:00 | Portmore United v Cavalier | W | 2-1 |
| Jamaica - Premier League | 2019/11/03 22:00 | Cavalier v Portmore United | D | 0-0 |
| Jamaica - Premier League | 2019/02/10 20:00 | Portmore United v Cavalier | W | 1-0 |
| Jamaica - Premier League | 2018/12/23 22:00 | Cavalier v Portmore United | L | 2-1 |
| Jamaica - Premier League | 2018/10/07 22:00 | Cavalier v Portmore United | W | 0-2 |
Home History
| Jamaica - Premier League | 2023/01/08 20:00 | Tivoli Gardens v Portmore United | D | 0-0 |
| Jamaica - Premier League | 2023/01/03 00:30 | Portmore United v Harbour View FC | W | 1-0 |
| Jamaica - Premier League | 2022/12/28 18:00 | Faulkland FC v Portmore United | W | 1-3 |
| Jamaica - Premier League | 2022/12/21 22:15 | Portmore United v Dunbeholden FC | D | 0-0 |
| Jamaica - Premier League | 2022/12/05 22:00 | Chapelton Maroons FC v Portmore United | W | 0-1 |
| Jamaica - Premier League | 2022/11/22 00:30 | Mount Pleasant FA v Portmore United | D | 0-0 |
| Jamaica - Premier League | 2022/11/17 20:15 | Arnett Gardens v Portmore United | D | 1-1 |
| Jamaica - Premier League | 2022/11/08 00:30 | Portmore United v Vere United | D | 0-0 |
Away History
| Jamaica - Premier League | 2023/01/09 22:00 | Humble Lions v Cavalier | W | 1-2 |
| Jamaica - Premier League | 2023/01/01 20:00 | Cavalier v Tivoli Gardens | W | 3-0 |
| Jamaica - Premier League | 2022/12/26 22:00 | Harbour View FC v Cavalier | D | 1-1 |
| Jamaica - Premier League | 2022/12/21 20:00 | Cavalier v Faulkland FC | W | 4-0 |
| Jamaica - Premier League | 2022/12/04 20:00 | Cavalier v Mount Pleasant FA | L | 0-1 |
| Jamaica - Premier League | 2022/11/20 22:30 | Dunbeholden FC v Cavalier | W | 1-2 |
| Jamaica - Premier League | 2022/11/06 22:30 | Chapelton Maroons FC v Cavalier | W | 0-3 |
| Jamaica - Premier League | 2022/10/30 20:00 | Vere United v Cavalier | W | 0-3 |
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