Head to Head
| 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 | 2019/03/17 20:30 | Montego Bay Utd v Portmore United | W | 1-5 |
| Jamaica Premier League | 2019/03/14 20:30 | Portmore United v Waterhouse | D | 0-0 |
| Jamaica Premier League | 2019/03/11 00:00 | Tivoli Gardens v Portmore United | L | 3-2 |
| Jamaica Premier League | 2019/03/03 20:30 | UWI FC v Portmore United | W | 0-1 |
| Jamaica Premier League | 2019/02/24 20:00 | Portmore United v Arnett Gardens | W | 3-0 |
| Jamaica Premier League | 2019/02/17 20:00 | Reno FC v Portmore United | W | 2-4 |
| Jamaica Premier League | 2019/02/10 20:00 | Portmore United v Cavalier | W | 1-0 |
| Jamaica Premier League | 2019/02/03 20:00 | Humble Lions v Portmore United | W | 0-2 |
Away History
| Jamaica Premier League | 2019/03/17 20:30 | Dunbeholden FC v UWI FC | L | 0-2 |
| Jamaica Premier League | 2019/03/14 20:30 | Arnett Gardens v Dunbeholden FC | D | 0-0 |
| Jamaica Premier League | 2019/03/10 20:30 | Dunbeholden FC v Reno FC | W | 3-0 |
| Jamaica Premier League | 2019/03/03 22:00 | Cavalier v Dunbeholden FC | D | 1-1 |
| Jamaica Premier League | 2019/02/24 20:00 | Dunbeholden FC v Humble Lions | W | 2-1 |
| Jamaica Premier League | 2019/02/18 00:00 | Harbour View FC v Dunbeholden FC | D | 1-1 |
| Jamaica Premier League | 2019/02/10 20:00 | Dunbeholden FC v Mount Pleasant FA | L | 1-2 |
| Jamaica Premier League | 2019/02/03 20:00 | Dunbeholden FC v Tivoli Gardens | D | 1-1 |