Head to Head
| Jamaica karikas | 2023/05/27 01:00 | Cavalier v Portmore United | W | 0-2 |
| Jamaica Premier League | 2023/04/16 20:00 | Cavalier v Portmore United | L | 2-0 |
| Jamaica Premier League | 2023/01/15 20:00 | Portmore United v Cavalier | L | 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 | 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 |
Home History
| Jamaica Premier League | 2023/12/10 23:00 | Waterhouse v Portmore United | D | 1-1 |
| Jamaica Premier League | 2023/12/03 20:00 | Montego Bay Utd v Portmore United | L | 3-2 |
| Jamaica Premier League | 2023/11/28 00:30 | Portmore United v Tivoli Gardens | D | 0-0 |
| Jamaica Premier League | 2023/11/22 22:30 | Harbour View FC v Portmore United | D | 1-1 |
| Jamaica Premier League | 2023/11/19 20:00 | Portmore United v Molynes United FC | W | 2-0 |
| Jamaica Premier League | 2023/11/12 20:00 | Dunbeholden FC v Portmore United | W | 0-2 |
| Jamaica Premier League | 2023/11/05 20:00 | Portmore United v Treasure Beach FC | W | 3-1 |
| Jamaica Premier League | 2023/10/22 20:30 | Mount Pleasant FA v Portmore United | L | 1-0 |
Away History
| Jamaica Premier League | 2023/12/12 00:30 | Cavalier v Mount Pleasant FA | W | 2-1 |
| CONCACAFi Kariibi karikas | 2023/12/07 00:00 | Cavalier v Robin Hood FC | L | 0-2 |
| CFU Kariibi karikas | 2023/11/30 23:00 | Robin Hood FC v Cavalier | L | 1-0 |
| Jamaica Premier League | 2023/11/23 20:00 | Vere United v Cavalier | W | 1-3 |
| Jamaica Premier League | 2023/11/19 18:00 | Lime Hall v Cavalier | D | 1-1 |
| Jamaica Premier League | 2023/11/14 00:30 | Cavalier v Waterhouse | D | 1-1 |
| Jamaica Premier League | 2023/11/09 20:00 | Harbour View FC v Cavalier | W | 1-3 |
| Jamaica Premier League | 2023/11/05 20:00 | Montego Bay Utd v Cavalier | L | 1-0 |
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