Head to Head
| 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 |
| 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 |
Home History
| Jamaica Premier League | 2023/11/05 20:00 | Mount Pleasant FA v Dunbeholden FC | L | 3-0 |
| Jamaica Premier League | 2023/10/24 00:30 | Arnett Gardens v Dunbeholden FC | D | 0-0 |
| CFU Caribbean Cup | 2023/09/29 00:06 | Dunbeholden FC v Cibao FC | W | 2-1 |
| CFU Caribbean Cup | 2023/09/22 00:06 | Dunbeholden FC v Robin Hood FC | L | 0-2 |
| CFU Caribbean Cup | 2023/08/31 00:06 | Atletico Pantoja v Dunbeholden FC | D | 1-1 |
| CFU Club Championship | 2023/08/23 22:06 | Harbour View FC v Dunbeholden FC | L | 1-0 |
| Jamaica Cup | 2023/05/26 22:00 | Harbour View FC v Dunbeholden FC | W | 0-1 |
| Jamaica Premier League | 2023/05/23 01:00 | Mount Pleasant FA v Dunbeholden FC | L | 3-0 |
Away History
| Jamaica Premier League | 2023/11/05 20:00 | Portmore United v Treasure Beach FC | W | 3-1 |
| Jamaica Premier League | 2023/10/22 20:30 | Mount Pleasant FA v Portmore United | L | 1-0 |
| Jamaica Cup | 2023/05/27 01:00 | Cavalier v Portmore United | W | 0-2 |
| Jamaica Cup | 2023/05/20 01:00 | Portmore United v Harbour View FC | D | 1-1 |
| Jamaica Cup | 2023/05/12 22:30 | Harbour View FC v Portmore United | D | 2-2 |
| Jamaica Premier League | 2023/05/07 20:15 | Molynes United FC v Portmore United | W | 0-3 |
| Jamaica Premier League | 2023/04/30 21:00 | Portmore United v Waterhouse | D | 1-1 |
| Jamaica Premier League | 2023/04/23 21:00 | Portmore United v Humble Lions | D | 1-1 |