Head to Head
| Jamaica Premier League | 2024/03/18 22:00 | Cavalier v Portmore United | L | 0-1 |
| Jamaica Premier League | 2023/12/17 20:00 | Portmore United v Cavalier | L | 1-0 |
| Jamaica Cup | 2023/05/27 01:00 | Cavalier v Portmore United | L | 0-2 |
| Jamaica Premier League | 2023/04/16 20:00 | Cavalier v Portmore United | W | 2-0 |
| Jamaica Premier League | 2023/01/15 20:00 | Portmore United v Cavalier | W | 1-2 |
| 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 | L | 0-1 |
| Jamaica Premier League | 2021/09/03 18:00 | Cavalier v Portmore United | W | 1-0 |
Home History
| CONCACAF Caribbean Cup | 2024/09/18 00:00 | Cavalier v Real Hope FA | L | 1-2 |
| CONCACAF Caribbean Cup | 2024/08/30 00:00 | Cavalier v Police FC TT | W | 4-1 |
| CONCACAF Caribbean Cup | 2024/08/20 22:00 | Mount Pleasant FA v Cavalier | W | 0-2 |
| Jamaica Premier League | 2024/05/19 23:30 | Mount Pleasant FA v Cavalier | W | 4-5 |
| Jamaica Premier League | 2024/05/13 01:00 | Cavalier v Arnett Gardens | W | 3-1 |
| Jamaica Premier League | 2024/05/05 22:00 | Arnett Gardens v Cavalier | D | 1-1 |
| Jamaica Premier League | 2024/04/07 20:30 | Cavalier v Molynes United FC | W | 6-0 |
| Jamaica Premier League | 2024/03/31 20:30 | Dunbeholden FC v Cavalier | W | 2-4 |
Away History
| Jamaica Premier League | 2024/09/15 21:00 | Portmore United v Mount Pleasant FA | L | 0-2 |
| Jamaica Premier League | 2024/04/29 22:00 | Portmore United v Arnett Gardens | L | 0-1 |
| Jamaica Premier League | 2024/04/23 00:30 | Arnett Gardens v Portmore United | D | 1-1 |
| Jamaica Premier League | 2024/04/07 20:30 | Portmore United v Humble Lions | W | 2-0 |
| Jamaica Premier League | 2024/03/31 23:00 | Arnett Gardens v Portmore United | D | 1-1 |
| Jamaica Premier League | 2024/03/24 18:00 | Portmore United v Vere United | L | 0-1 |
| Jamaica Premier League | 2024/03/18 22:00 | Cavalier v Portmore United | W | 0-1 |
| Jamaica Premier League | 2024/03/10 20:30 | Portmore United v Waterhouse | D | 0-0 |