Head to Head
| Jamaica Premier League | 2024/12/29 20:00 | Portmore United v Cavalier | D | 1-1 |
| Jamaica Premier League | 2024/09/22 22:30 | Cavalier v Portmore United | W | 2-1 |
| 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 |
Home History
| CONCACAF Champions Cup | 2025/03/07 01:00 | Inter Miami CF v Cavalier | L | 2-0 |
| Jamaica Premier League | 2025/02/23 20:00 | Chapelton Maroons FC v Cavalier | W | 1-2 |
| Jamaica Premier League | 2025/02/20 21:30 | Cavalier v Harbour View FC | L | 0-1 |
| Jamaica Premier League | 2025/02/16 18:00 | Molynes United FC v Cavalier | W | 0-3 |
| Jamaica Premier League | 2025/02/13 21:30 | Cavalier v Montego Bay Utd | D | 1-1 |
| Jamaica Premier League | 2025/02/03 22:00 | Vere United v Cavalier | W | 1-2 |
| Jamaica Premier League | 2025/01/30 21:30 | Cavalier v Tivoli Gardens | D | 0-0 |
| Jamaica Premier League | 2025/01/27 00:30 | Cavalier v Arnett Gardens | D | 2-2 |
Away History
| Jamaica Premier League | 2025/02/23 22:30 | Waterhouse v Portmore United | L | 1-0 |
| Jamaica Premier League | 2025/02/21 00:00 | Arnett Gardens v Portmore United | D | 0-0 |
| Jamaica Premier League | 2025/02/16 20:00 | Racing United FC v Portmore United | D | 1-1 |
| Jamaica Premier League | 2025/02/12 20:00 | Portmore United v Dunbeholden FC | D | 0-0 |
| Jamaica Premier League | 2025/02/02 20:00 | Portmore United v Humble Lions | W | 2-1 |
| Jamaica Premier League | 2025/01/30 20:00 | Molynes United FC v Portmore United | D | 0-0 |
| Jamaica Premier League | 2025/01/26 20:00 | Portmore United v Montego Bay Utd | D | 0-0 |
| Jamaica Premier League | 2025/01/22 20:00 | Chapelton Maroons FC v Portmore United | W | 0-3 |
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