Head to Head
| Jamaica Premier League | 2019/03/03 20:30 | UWI FC v Portmore United | W | 0-1 |
| Jamaica Premier League | 2019/01/13 20:00 | Portmore United v UWI FC | L | 1-2 |
| Jamaica Premier League | 2018/10/28 20:00 | Portmore United v UWI FC | D | 1-1 |
| Jamaica Premier League | 2018/02/25 20:00 | UWI FC v Portmore United | L | 3-0 |
| Jamaica Premier League | 2017/12/28 20:00 | Portmore United v UWI FC | W | 5-1 |
| Jamaica Premier League | 2017/11/01 20:00 | Portmore United v UWI FC | L | 0-1 |
| Jamaica Premier League | 2017/05/28 20:00 | UWI FC v Portmore United | W | 0-2 |
| Jamaica Premier League | 2017/05/07 20:00 | Portmore United v UWI FC | L | 1-2 |
Home History
| Jamaica Premier League | 2019/10/06 20:30 | Tivoli Gardens v Portmore United | D | 1-1 |
| Jamaica Premier League | 2019/09/29 20:30 | Portmore United v Humble Lions | W | 2-0 |
| 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 |
Away History
| Jamaica Premier League | 2019/10/06 20:30 | UWI FC v Waterhouse | L | 0-2 |
| Jamaica Premier League | 2019/10/01 01:30 | Cavalier v UWI FC | L | 4-0 |
| Jamaica Premier League | 2019/09/24 01:30 | UWI FC v Mount Pleasant FA | D | 0-0 |
| Jamaica Premier League | 2019/09/17 01:35 | Arnett Gardens v UWI FC | D | 0-0 |
| Jamaica Premier League | 2019/09/08 20:30 | Molynes United FC v UWI FC | L | 3-2 |
| Jamaica Premier League | 2019/09/01 20:30 | UWI FC v Tivoli Gardens | W | 4-0 |
| Jamaica Premier League | 2019/03/31 20:00 | Mount Pleasant FA v UWI FC | L | 1-0 |
| Jamaica Premier League | 2019/03/24 22:30 | UWI FC v Mount Pleasant FA | D | 2-2 |
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