Head to Head
| Jamaica Premier League | 2025/02/12 20:00 | Portmore United v Dunbeholden FC | D | 0-0 |
| Jamaica Premier League | 2024/12/01 20:00 | Dunbeholden FC v Portmore United | D | 3-3 |
| Jamaica Premier League | 2024/02/04 20:00 | Portmore United v Dunbeholden FC | D | 1-1 |
| Jamaica Premier League | 2023/11/12 20:00 | Dunbeholden FC v Portmore United | L | 0-2 |
| Jamaica Premier League | 2023/03/19 22:30 | Dunbeholden FC v Portmore United | L | 1-3 |
| Jamaica Premier League | 2022/12/21 22:15 | Portmore United v Dunbeholden FC | D | 0-0 |
| Jamaica Premier League | 2022/05/29 20:00 | Dunbeholden FC v Portmore United | W | 1-0 |
| Jamaica Premier League | 2022/03/14 22:15 | Portmore United v Dunbeholden FC | W | 2-3 |
Home History
| Jamaica Premier League | 2025/02/23 20:00 | Dunbeholden FC v Humble Lions | W | 3-2 |
| Jamaica Premier League | 2025/02/19 20:00 | Molynes United FC v Dunbeholden FC | W | 0-1 |
| Jamaica Premier League | 2025/02/16 20:00 | Dunbeholden FC v Waterhouse | W | 1-0 |
| Jamaica Premier League | 2025/02/12 20:00 | Portmore United v Dunbeholden FC | D | 0-0 |
| Jamaica Premier League | 2025/02/02 20:00 | Dunbeholden FC v Montego Bay Utd | W | 2-0 |
| Jamaica Premier League | 2025/01/29 21:30 | Chapelton Maroons FC v Dunbeholden FC | W | 1-3 |
| Jamaica Premier League | 2025/01/26 20:00 | Harbour View FC v Dunbeholden FC | L | 4-1 |
| Jamaica Premier League | 2025/01/22 20:00 | Dunbeholden FC v Vere United | D | 1-1 |
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 |