Head to Head
| Jamaica Premier League | 2020/01/30 20:00 | Dunbeholden FC v Portmore United | W | 1-4 |
| Jamaica Premier League | 2019/12/01 20:00 | Portmore United v Dunbeholden FC | L | 1-2 |
| Jamaica Premier League | 2019/09/15 20:30 | Portmore United v Dunbeholden FC | L | 0-1 |
| Jamaica Premier League | 2019/03/20 20:30 | Portmore United v Dunbeholden FC | W | 2-0 |
| Jamaica Premier League | 2018/12/02 20:00 | Dunbeholden FC v Portmore United | W | 0-1 |
| Jamaica Premier League | 2018/11/18 20:00 | Dunbeholden FC v Portmore United | W | 2-3 |
Home History
| Jamaica Premier League | 2020/03/08 20:30 | UWI FC v Portmore United | W | 1-3 |
| Jamaica Premier League | 2020/03/05 20:00 | Portmore United v Harbour View FC | D | 0-0 |
| Jamaica Premier League | 2020/03/01 20:30 | Portmore United v Tivoli Gardens | L | 0-1 |
| CONCACAF Champions Cup | 2020/02/26 03:15 | Cruz Azul v Portmore United | L | 4-0 |
| CONCACAF Champions Cup | 2020/02/19 01:00 | Portmore United v Cruz Azul | L | 1-2 |
| CFU Club Championship | 2020/02/09 23:00 | Portmore United v Arcahaie FC | L | 0-1 |
| CFU Club Championship | 2020/02/06 00:00 | Portmore United v Atletico Pantoja | L | 0-4 |
| Jamaica Premier League | 2020/01/30 20:00 | Dunbeholden FC v Portmore United | W | 1-4 |
Away History
| Jamaica Premier League | 2020/03/08 22:00 | Humble Lions v Dunbeholden FC | D | 0-0 |
| Jamaica Premier League | 2020/03/01 20:30 | Dunbeholden FC v Harbour View FC | W | 2-0 |
| Jamaica Premier League | 2020/02/23 20:30 | Molynes United FC v Dunbeholden FC | W | 2-4 |
| Jamaica Premier League | 2020/02/16 20:00 | Vere United v Dunbeholden FC | D | 1-1 |
| Jamaica Premier League | 2020/01/30 20:00 | Dunbeholden FC v Portmore United | L | 1-4 |
| 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 |