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 |