Head to Head
| 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 |
| Jamaica - Premier League | 2021/06/27 16:00 | Portmore United v Dunbeholden FC | L | 2-0 |
| Jamaica - Premier League | 2020/01/30 20:00 | Dunbeholden FC v Portmore United | L | 1-4 |
| Jamaica - Premier League | 2019/12/01 20:00 | Portmore United v Dunbeholden FC | W | 1-2 |
| Jamaica - Premier League | 2019/09/15 20:30 | Portmore United v Dunbeholden FC | W | 0-1 |
| Jamaica - Premier League | 2019/03/20 20:30 | Portmore United v Dunbeholden FC | L | 2-0 |
Home History
| Jamaica - Premier League | 2023/03/12 20:00 | Cavalier v Dunbeholden FC | L | 3-1 |
| Jamaica - Premier League | 2023/03/05 20:00 | Dunbeholden FC v Tivoli Gardens | W | 4-1 |
| Jamaica - Premier League | 2023/02/27 22:00 | Harbour View FC v Dunbeholden FC | L | 2-0 |
| Jamaica - Premier League | 2023/02/19 18:00 | Dunbeholden FC v Faulkland FC | W | 4-2 |
| Jamaica - Premier League | 2023/02/14 00:30 | Dunbeholden FC v Humble Lions | L | 1-2 |
| Jamaica - Premier League | 2023/02/05 20:00 | Mount Pleasant FA v Dunbeholden FC | L | 3-0 |
| Jamaica - Premier League | 2023/01/29 18:00 | Dunbeholden FC v Chapelton Maroons FC | D | 0-0 |
| Jamaica - Premier League | 2023/01/23 22:00 | Vere United v Dunbeholden FC | W | 0-1 |
Away History
| Jamaica - Premier League | 2023/03/06 22:00 | Portmore United v Chapelton Maroons FC | D | 0-0 |
| Jamaica - Premier League | 2023/02/26 20:00 | Vere United v Portmore United | W | 0-2 |
| Jamaica - Premier League | 2023/02/19 20:00 | Portmore United v Arnett Gardens | L | 1-2 |
| Jamaica - Premier League | 2023/02/12 20:15 | Montego Bay Utd v Portmore United | D | 1-1 |
| Jamaica - Premier League | 2023/02/06 22:00 | Portmore United v Molynes United FC | D | 1-1 |
| Jamaica - Premier League | 2023/01/29 21:00 | Waterhouse v Portmore United | D | 1-1 |
| Jamaica - Premier League | 2023/01/22 20:00 | Humble Lions v Portmore United | L | 1-0 |
| Jamaica - Premier League | 2023/01/15 20:00 | Portmore United v Cavalier | L | 1-2 |