Head to Head
| Jamaica Premier League | 2022/01/30 20:15 | Cavalier v Portmore United | W | 0-1 |
| Jamaica Premier League | 2021/09/03 18:00 | Cavalier v Portmore United | L | 1-0 |
| Jamaica Premier League | 2019/12/12 20:00 | Portmore United v Cavalier | W | 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 | W | 1-0 |
| Jamaica Premier League | 2018/12/23 22:00 | Cavalier v Portmore United | L | 2-1 |
| Jamaica Premier League | 2018/10/07 22:00 | Cavalier v Portmore United | W | 0-2 |
| Jamaica Premier League | 2018/04/15 20:00 | Portmore United v Cavalier | W | 3-0 |
Home History
| Jamaica Premier League | 2022/04/10 22:15 | Arnett Gardens v Portmore United | L | 2-1 |
| Jamaica Premier League | 2022/04/04 22:00 | Portmore United v Tivoli Gardens | D | 1-1 |
| Jamaica Premier League | 2022/03/27 20:00 | Mount Pleasant FA v Portmore United | W | 0-2 |
| Jamaica Premier League | 2022/03/21 22:15 | Portmore United v Molynes United FC | L | 0-2 |
| Jamaica Premier League | 2022/03/14 22:15 | Portmore United v Dunbeholden FC | L | 2-3 |
| Jamaica Premier League | 2022/03/07 20:15 | Montego Bay Utd v Portmore United | W | 0-1 |
| Jamaica Premier League | 2022/02/27 20:15 | Portmore United v Vere United | W | 2-1 |
| Jamaica Premier League | 2022/02/21 18:00 | Harbour View FC v Portmore United | L | 2-0 |
Away History
| Jamaica Premier League | 2022/04/12 00:30 | Waterhouse v Cavalier | L | 3-2 |
| Jamaica Premier League | 2022/04/03 22:15 | Cavalier v Arnett Gardens | W | 1-0 |
| Jamaica Premier League | 2022/03/26 20:00 | Tivoli Gardens v Cavalier | W | 1-3 |
| Jamaica Premier League | 2022/03/20 20:00 | Cavalier v Mount Pleasant FA | D | 0-0 |
| Jamaica Premier League | 2022/03/14 20:00 | Molynes United FC v Cavalier | W | 0-2 |
| Jamaica Premier League | 2022/03/07 18:00 | Cavalier v Dunbeholden FC | L | 1-2 |
| Jamaica Premier League | 2022/02/28 20:15 | Cavalier v Montego Bay Utd | W | 3-0 |
| Jamaica Premier League | 2022/02/19 18:00 | Vere United v Cavalier | L | 1-0 |