[11] Portmore United 0-1 Dunbeholden FC [10] 2019-09-15 20:30
Stadium: Ferdi Neita Sports Complex Round: 3
Head to Head
| 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 | 2019/09/08 20:30 | Vere United v Portmore United | L | 2-0 |
| Jamaica Premier League | 2019/09/03 01:30 | Portmore United v Molynes United FC | L | 0-3 |
| CFU Club Championship | 2019/05/17 01:00 | Portmore United v Waterhouse | D | 1-1 |
| CFU Club Championship | 2019/05/15 01:00 | Portmore United v AS Capoise | W | 1-0 |
| CFU Club Championship | 2019/05/12 22:30 | Portmore United v Real Hope FA | W | 1-0 |
| Jamaica Play-Offs | 2019/04/30 01:35 | Portmore United v Waterhouse | W | 1-0 |
| Jamaica Premier League | 2019/04/16 01:35 | Portmore United v Mount Pleasant FA | D | 1-1 |
| Jamaica Premier League | 2019/04/08 22:30 | Mount Pleasant FA v Portmore United | W | 1-2 |
Away History
| Jamaica Premier League | 2019/09/08 20:30 | Dunbeholden FC v Waterhouse | L | 0-1 |
| Jamaica Premier League | 2019/09/01 22:00 | Cavalier v Dunbeholden FC | L | 3-1 |
| Jamaica Premier League | 2019/03/20 20:30 | Portmore United v Dunbeholden FC | L | 2-0 |
| 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 |