Head to Head
| Jamaica Premier League | 2024/03/18 22:00 | Cavalier v Portmore United | L | 0-1 |
| 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 |
| 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 |
| Jamaica Premier League | 2018/12/23 22:00 | Cavalier v Portmore United | W | 2-1 |
| Jamaica Premier League | 2018/10/07 22:00 | Cavalier v Portmore United | L | 0-2 |
| Jamaica Premier League | 2018/04/15 20:00 | Portmore United v Cavalier | L | 3-0 |
| Jamaica Premier League | 2018/04/08 23:00 | Cavalier v Portmore United | D | 0-0 |
| Jamaica Premier League | 2018/01/21 22:00 | Cavalier v Portmore United | W | 3-0 |
| Jamaica Premier League | 2017/11/28 01:35 | Cavalier v Portmore United | D | 0-0 |
| Jamaica Premier League | 2017/09/25 22:45 | Portmore United v Cavalier | L | 1-0 |
| Jamaica Premier League | 2016/03/08 01:30 | Cavalier v Portmore United | L | 0-1 |
| Jamaica Premier League | 2015/12/09 22:00 | Cavalier v Portmore United | W | 2-1 |
| Jamaica Premier League | 2015/10/04 21:00 | Portmore United v Cavalier | L | 1-0 |