[12] Portmore United 2-0 Humble Lions [3] 2019-09-29 20:30
Stadium: Ferdi Neita Sports Complex Round: 5
Head to Head
| Jamaica Premier League | 2019/02/03 20:00 | Humble Lions v Portmore United | W | 0-2 |
| Jamaica Premier League | 2018/12/13 20:00 | Humble Lions v Portmore United | D | 1-1 |
| Jamaica Premier League | 2018/09/30 20:30 | Portmore United v Humble Lions | D | 0-0 |
| Jamaica Premier League | 2018/02/22 20:30 | Humble Lions v Portmore United | W | 0-1 |
| Jamaica Premier League | 2018/01/17 20:00 | Portmore United v Humble Lions | W | 2-0 |
| Jamaica Premier League | 2017/10/22 20:30 | Portmore United v Humble Lions | W | 3-0 |
| Jamaica Premier League | 2017/03/30 20:30 | Humble Lions v Portmore United | D | 3-3 |
| Jamaica Premier League | 2016/11/30 20:00 | Humble Lions v Portmore United | W | 0-1 |
Home History
| Jamaica Premier League | 2019/09/23 00:00 | Harbour View FC v Portmore United | W | 1-2 |
| Jamaica Premier League | 2019/09/15 20:30 | Portmore United v Dunbeholden FC | L | 0-1 |
| 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 |
Away History
| Jamaica Premier League | 2019/09/22 20:30 | Humble Lions v Waterhouse | D | 0-0 |
| Jamaica Premier League | 2019/09/15 22:00 | Cavalier v Humble Lions | D | 1-1 |
| Jamaica Premier League | 2019/09/08 20:30 | Humble Lions v Mount Pleasant FA | D | 1-1 |
| Jamaica Premier League | 2019/09/02 00:00 | Arnett Gardens v Humble Lions | W | 1-3 |
| Jamaica Premier League | 2019/03/17 20:30 | Humble Lions v Cavalier | D | 1-1 |
| Jamaica Premier League | 2019/03/14 20:30 | Humble Lions v Tivoli Gardens | W | 2-0 |
| Jamaica Premier League | 2019/03/11 00:00 | Harbour View FC v Humble Lions | L | 1-0 |
| Jamaica Premier League | 2019/03/03 20:30 | Humble Lions v Mount Pleasant FA | L | 0-1 |