Face à face
| Jamaïque - Premier League | 2023/01/15 20:00 | Portmore United v Cavalier | W | 1-2 |
| Jamaïque - Premier League | 2022/04/17 20:00 | Portmore United v Cavalier | D | 0-0 |
| Jamaïque - Premier League | 2022/01/30 20:15 | Cavalier v Portmore United | L | 0-1 |
| Jamaïque - Premier League | 2021/09/03 18:00 | Cavalier v Portmore United | W | 1-0 |
| Jamaïque - Premier League | 2019/12/12 20:00 | Portmore United v Cavalier | L | 2-1 |
| Jamaïque - Premier League | 2019/11/03 22:00 | Cavalier v Portmore United | D | 0-0 |
| Jamaïque - Premier League | 2019/02/10 20:00 | Portmore United v Cavalier | L | 1-0 |
| Jamaïque - Premier League | 2018/12/23 22:00 | Cavalier v Portmore United | W | 2-1 |
Home History
| Jamaïque - Premier League | 2023/04/10 22:00 | Cavalier v Humble Lions | W | 1-0 |
| Jamaïque - Premier League | 2023/04/02 20:00 | Tivoli Gardens v Cavalier | W | 0-1 |
| Jamaïque - Premier League | 2023/03/26 22:30 | Cavalier v Harbour View FC | L | 1-2 |
| Jamaïque - Premier League | 2023/03/21 00:30 | Faulkland FC v Cavalier | D | 2-2 |
| Jamaïque - Premier League | 2023/03/12 20:00 | Cavalier v Dunbeholden FC | W | 3-1 |
| Jamaïque - Premier League | 2023/03/07 00:30 | Mount Pleasant FA v Cavalier | D | 2-2 |
| Jamaïque - Premier League | 2023/02/26 22:30 | Cavalier v Chapelton Maroons FC | W | 4-1 |
| Jamaïque - Premier League | 2023/02/21 00:30 | Cavalier v Vere United | W | 1-0 |
Away History
| Jamaïque - Premier League | 2023/04/09 21:00 | Portmore United v Tivoli Gardens | W | 2-1 |
| Jamaïque - Premier League | 2023/04/06 21:00 | Portmore United v Mount Pleasant FA | D | 0-0 |
| Jamaïque - Premier League | 2023/04/02 22:30 | Harbour View FC v Portmore United | W | 0-1 |
| Jamaïque - Premier League | 2023/03/26 21:00 | Portmore United v Faulkland FC | W | 4-0 |
| Jamaïque - Premier League | 2023/03/19 22:30 | Dunbeholden FC v Portmore United | W | 1-3 |
| Jamaïque - Premier League | 2023/03/06 22:00 | Portmore United v Chapelton Maroons FC | D | 0-0 |
| Jamaïque - Premier League | 2023/02/26 20:00 | Vere United v Portmore United | W | 0-2 |
| Jamaïque - Premier League | 2023/02/19 20:00 | Portmore United v Arnett Gardens | L | 1-2 |