Head to Head
| 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 |
| Jamaica Premier League | 2019/12/12 20:00 | Portmore United v Cavalier | L | 2-1 |
Home History
| Jamaica Premier League | 2024/03/10 20:30 | Mount Pleasant FA v Cavalier | L | 2-0 |
| Jamaica Premier League | 2024/03/08 00:00 | Arnett Gardens v Cavalier | D | 2-2 |
| Jamaica Premier League | 2024/03/04 22:00 | Cavalier v Humble Lions | D | 1-1 |
| CONCACAF Champions Cup | 2024/02/29 00:00 | FC Cincinnati v Cavalier | L | 4-0 |
| CONCACAF Champions Cup | 2024/02/23 02:00 | Cavalier v FC Cincinnati | L | 0-2 |
| Jamaica Premier League | 2024/02/18 21:00 | Cavalier v Vere United | W | 2-0 |
| Jamaica Premier League | 2024/02/11 20:30 | Cavalier v Lime Hall | W | 4-0 |
| Jamaica Premier League | 2024/02/04 21:00 | Waterhouse v Cavalier | W | 0-1 |
Away History
| Jamaica Premier League | 2024/03/10 20:30 | Portmore United v Waterhouse | D | 0-0 |
| Jamaica Premier League | 2024/03/03 20:30 | Portmore United v Montego Bay Utd | D | 1-1 |
| Jamaica Premier League | 2024/02/25 21:00 | Tivoli Gardens v Portmore United | D | 0-0 |
| Jamaica Premier League | 2024/02/18 20:30 | Portmore United v Harbour View FC | W | 1-0 |
| Jamaica Premier League | 2024/02/11 23:00 | Molynes United FC v Portmore United | D | 2-2 |
| Jamaica Premier League | 2024/02/04 20:00 | Portmore United v Dunbeholden FC | D | 1-1 |
| Jamaica Premier League | 2024/01/28 20:00 | Treasure Beach FC v Portmore United | W | 1-3 |
| Jamaica Premier League | 2024/01/21 18:00 | Lime Hall v Portmore United | W | 0-2 |