Head to Head
| Jamaica Premier League | 2024/09/22 22:30 | Cavalier v Portmore United | L | 2-1 |
| Jamaica Premier League | 2024/03/18 22:00 | Cavalier v Portmore United | W | 0-1 |
| Jamaica Premier League | 2023/12/17 20:00 | Portmore United v Cavalier | W | 1-0 |
| Jamaica Cup | 2023/05/27 01:00 | Cavalier v Portmore United | W | 0-2 |
| Jamaica Premier League | 2023/04/16 20:00 | Cavalier v Portmore United | L | 2-0 |
| Jamaica Premier League | 2023/01/15 20:00 | Portmore United v Cavalier | L | 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 | W | 0-1 |
Home History
| Jamaica Premier League | 2024/12/22 20:00 | Mount Pleasant FA v Portmore United | L | 1-0 |
| Jamaica Premier League | 2024/12/08 20:00 | Portmore United v Racing United FC | D | 1-1 |
| Jamaica Premier League | 2024/12/01 20:00 | Dunbeholden FC v Portmore United | D | 3-3 |
| Jamaica Premier League | 2024/11/24 20:00 | Portmore United v Waterhouse | D | 0-0 |
| Jamaica Premier League | 2024/11/17 20:15 | Portmore United v Arnett Gardens | L | 0-1 |
| Jamaica Premier League | 2024/11/10 20:00 | Humble Lions v Portmore United | W | 0-1 |
| Jamaica Premier League | 2024/11/03 20:00 | Portmore United v Molynes United FC | W | 4-0 |
| Jamaica Premier League | 2024/10/27 22:30 | Montego Bay Utd v Portmore United | D | 0-0 |
Away History
| Jamaica Premier League | 2024/12/22 22:30 | Cavalier v Humble Lions | W | 3-1 |
| Jamaica Premier League | 2024/12/19 00:30 | Montego Bay Utd v Cavalier | D | 1-1 |
| Jamaica Premier League | 2024/12/15 21:00 | Cavalier v Chapelton Maroons FC | L | 1-3 |
| Jamaica Premier League | 2024/12/13 00:00 | Arnett Gardens v Cavalier | W | 1-2 |
| Jamaica Premier League | 2024/12/08 21:00 | Cavalier v Molynes United FC | W | 5-1 |
| CONCACAF Caribbean Cup | 2024/12/04 00:00 | Cibao FC v Cavalier | L | 2-1 |
| CONCACAF Caribbean Cup | 2024/11/27 01:00 | Cavalier v Cibao FC | W | 1-0 |
| Jamaica Premier League | 2024/11/20 20:00 | Racing United FC v Cavalier | L | 1-0 |