Head to Head
| 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 |
| 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 |
Home History
| Jamaica Cup | 2023/05/19 22:00 | Dunbeholden FC v Cavalier | W | 0-3 |
| Jamaica Cup | 2023/05/13 01:00 | Cavalier v Dunbeholden FC | W | 1-0 |
| Jamaica Premier League | 2023/05/07 20:15 | Montego Bay Utd v Cavalier | W | 1-2 |
| Jamaica Premier League | 2023/05/01 22:00 | Cavalier v Molynes United FC | W | 4-2 |
| Jamaica Premier League | 2023/04/23 21:15 | Waterhouse v Cavalier | L | 1-0 |
| Jamaica Cup | 2023/04/20 00:00 | Mount Pleasant FA v Cavalier | W | 0-1 |
| Jamaica Premier League | 2023/04/16 20:00 | Cavalier v Portmore United | W | 2-0 |
| Jamaica Premier League | 2023/04/10 22:00 | Cavalier v Humble Lions | W | 1-0 |
Away History
| Jamaica Cup | 2023/05/20 01:00 | Portmore United v Harbour View FC | D | 1-1 |
| Jamaica Cup | 2023/05/12 22:30 | Harbour View FC v Portmore United | D | 2-2 |
| Jamaica Premier League | 2023/05/07 20:15 | Molynes United FC v Portmore United | W | 0-3 |
| Jamaica Premier League | 2023/04/30 21:00 | Portmore United v Waterhouse | D | 1-1 |
| Jamaica Premier League | 2023/04/23 21:00 | Portmore United v Humble Lions | D | 1-1 |
| Jamaica Cup | 2023/04/20 21:00 | Molynes United FC v Portmore United | D | 2-2 |
| Jamaica Premier League | 2023/04/16 20:00 | Cavalier v Portmore United | L | 2-0 |
| Jamaica Premier League | 2023/04/09 21:00 | Portmore United v Tivoli Gardens | W | 2-1 |