Head to Head
| 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 |
| Jamaica Premier League | 2018/01/21 22:00 | Cavalier v Portmore United | W | 3-0 |
Home History
| Jamaica Premier League | 2021/08/27 20:30 | Cavalier v Mount Pleasant FA | L | 2-3 |
| Jamaica Premier League | 2021/08/14 17:00 | Molynes United FC v Cavalier | W | 1-3 |
| Jamaica Premier League | 2021/08/09 18:00 | Waterhouse v Cavalier | D | 2-2 |
| Jamaica Premier League | 2021/08/01 16:00 | Tivoli Gardens v Cavalier | D | 1-1 |
| Jamaica Premier League | 2021/07/17 18:00 | Arnett Gardens v Cavalier | W | 0-3 |
| Jamaica Premier League | 2021/07/11 18:00 | Cavalier v Dunbeholden FC | L | 0-1 |
| Jamaica Premier League | 2021/07/05 20:30 | Harbour View FC v Cavalier | D | 1-1 |
| Jamaica Premier League | 2021/06/26 20:30 | Cavalier v Humble Lions | W | 2-0 |
Away History
| 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 |
| Jamaica Premier League | 2021/07/19 20:30 | Tivoli Gardens v Portmore United | W | 1-3 |
| Jamaica Premier League | 2021/07/10 18:00 | Portmore United v Molynes United FC | W | 1-0 |
| Jamaica Premier League | 2021/07/06 20:30 | Vere United v Portmore United | L | 1-0 |
| Jamaica Premier League | 2021/06/27 16:00 | Portmore United v Dunbeholden FC | W | 2-0 |