Head to Head
| 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 |
| Jamaica Premier League | 2018/12/02 20:00 | Dunbeholden FC v Portmore United | L | 0-1 |
| Jamaica Premier League | 2018/11/18 20:00 | Dunbeholden FC v Portmore United | L | 2-3 |
Home History
| Jamaica Premier League | 2020/01/25 01:00 | Waterhouse v Dunbeholden FC | L | 3-1 |
| Jamaica Premier League | 2020/01/19 20:00 | Dunbeholden FC v Cavalier | W | 1-0 |
| Jamaica Premier League | 2020/01/12 20:00 | UWI FC v Dunbeholden FC | D | 0-0 |
| Jamaica Premier League | 2020/01/05 20:00 | Dunbeholden FC v Cavalier | W | 2-0 |
| Jamaica Premier League | 2019/12/29 20:00 | Molynes United FC v Dunbeholden FC | W | 2-3 |
| Jamaica Premier League | 2019/12/23 01:00 | Arnett Gardens v Dunbeholden FC | W | 0-3 |
| Jamaica Premier League | 2019/12/15 20:00 | Dunbeholden FC v Waterhouse | D | 1-1 |
| Jamaica Premier League | 2019/12/13 00:00 | Mount Pleasant FA v Dunbeholden FC | L | 2-1 |
Away History
| Jamaica Premier League | 2020/01/26 20:00 | Portmore United v Vere United | W | 5-0 |
| Jamaica Premier League | 2020/01/19 20:00 | Molynes United FC v Portmore United | W | 0-2 |
| Jamaica Premier League | 2020/01/12 20:00 | Portmore United v Arnett Gardens | W | 2-0 |
| Jamaica Premier League | 2020/01/05 20:00 | Portmore United v Humble Lions | L | 0-2 |
| Jamaica Premier League | 2019/12/30 00:00 | Harbour View FC v Portmore United | L | 1-0 |
| Jamaica Premier League | 2019/12/22 20:00 | Portmore United v Vere United | W | 3-1 |
| Jamaica Premier League | 2019/12/15 20:00 | UWI FC v Portmore United | W | 1-2 |
| Jamaica Premier League | 2019/12/12 20:00 | Portmore United v Cavalier | W | 2-1 |