Head to Head
| Jamaica Premier League | 2021/09/03 18:00 | Cavalier v Portmore United | W | 1-0 |
| Jamaica Premier League | 2019/12/12 20:00 | Portmore United v Cavalier | L | 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 | L | 1-0 |
| Jamaica Premier League | 2018/12/23 22:00 | Cavalier v Portmore United | W | 2-1 |
| Jamaica Premier League | 2018/10/07 22:00 | Cavalier v Portmore United | L | 0-2 |
| Jamaica Premier League | 2018/04/15 20:00 | Portmore United v Cavalier | L | 3-0 |
| Jamaica Premier League | 2018/04/08 23:00 | Cavalier v Portmore United | D | 0-0 |
Home History
| Jamaica Premier League | 2022/01/24 18:00 | Cavalier v Waterhouse | L | 0-3 |
| Jamaica Premier League | 2022/01/16 18:00 | Arnett Gardens v Cavalier | W | 1-2 |
| Jamaica Premier League | 2021/10/02 19:00 | Waterhouse v Cavalier | D | 1-1 |
| Jamaica Premier League | 2021/09/29 20:00 | Cavalier v Tivoli Gardens | D | 0-0 |
| Jamaica Premier League | 2021/09/25 17:00 | Tivoli Gardens v Cavalier | W | 0-1 |
| Jamaica Premier League | 2021/09/11 19:30 | Vere United v Cavalier | W | 0-1 |
| Jamaica Premier League | 2021/09/03 18:00 | Cavalier v Portmore United | W | 1-0 |
| Jamaica Premier League | 2021/08/27 20:30 | Cavalier v Mount Pleasant FA | L | 2-3 |
Away History
| Jamaica Premier League | 2022/01/25 18:00 | Portmore United v Arnett Gardens | L | 1-2 |
| Jamaica Premier League | 2022/01/17 20:15 | Tivoli Gardens v Portmore United | D | 1-1 |
| Jamaica Premier League | 2021/09/10 15:00 | Portmore United v Waterhouse | L | 0-1 |
| Jamaica Premier League | 2021/09/03 18:00 | Cavalier v Portmore United | L | 1-0 |
| Jamaica Premier League | 2021/08/16 18:00 | Arnett Gardens v Portmore United | L | 3-1 |
| Jamaica Premier League | 2021/08/08 16:00 | Portmore United v Mount Pleasant FA | L | 0-1 |
| Jamaica Premier League | 2021/07/31 20:30 | Harbour View FC v Portmore United | D | 1-1 |
| Jamaica Premier League | 2021/07/25 18:00 | Portmore United v Humble Lions | W | 3-0 |