Head to Head
| Jamaica Premier League | 2024/10/20 20:00 | Portmore United v Chapelton Maroons FC | L | 2-1 |
| Jamaica Premier League | 2023/03/06 22:00 | Portmore United v Chapelton Maroons FC | D | 0-0 |
| Jamaica Premier League | 2022/12/05 22:00 | Chapelton Maroons FC v Portmore United | L | 0-1 |
Home History
| Jamaica Premier League | 2025/01/19 20:00 | Humble Lions v Chapelton Maroons FC | L | 1-0 |
| Jamaica Premier League | 2025/01/12 20:00 | Chapelton Maroons FC v Molynes United FC | D | 0-0 |
| Jamaica Premier League | 2025/01/05 22:30 | Montego Bay Utd v Chapelton Maroons FC | L | 2-1 |
| Jamaica Premier League | 2024/12/30 00:00 | Arnett Gardens v Chapelton Maroons FC | D | 1-1 |
| Jamaica Premier League | 2024/12/22 20:00 | Chapelton Maroons FC v Harbour View FC | W | 1-0 |
| Jamaica Premier League | 2024/12/15 21:00 | Cavalier v Chapelton Maroons FC | W | 1-3 |
| Jamaica Premier League | 2024/12/08 20:00 | Vere United v Chapelton Maroons FC | L | 2-1 |
| Jamaica Premier League | 2024/12/01 20:00 | Chapelton Maroons FC v Tivoli Gardens | L | 2-3 |
Away History
| Jamaica Premier League | 2025/01/19 20:00 | Portmore United v Harbour View FC | W | 4-0 |
| Jamaica Premier League | 2025/01/12 20:00 | Vere United v Portmore United | W | 0-2 |
| Jamaica Premier League | 2025/01/06 22:00 | Tivoli Gardens v Portmore United | D | 1-1 |
| Jamaica Premier League | 2024/12/29 20:00 | Portmore United v Cavalier | D | 1-1 |
| Jamaica Premier League | 2024/12/22 20:00 | Mount Pleasant FA v Portmore United | L | 1-0 |
| Jamaica Premier League | 2024/12/08 20:00 | Portmore United v Racing United FC | D | 1-1 |
| Jamaica Premier League | 2024/12/01 20:00 | Dunbeholden FC v Portmore United | D | 3-3 |
| Jamaica Premier League | 2024/11/24 20:00 | Portmore United v Waterhouse | D | 0-0 |