Face à face
| Jamaïque - Premier League | 2019/12/15 20:00 | UWI Pelicans v Portmore United | L | 1-2 |
| Jamaïque - Premier League | 2019/10/13 20:30 | Portmore United v UWI Pelicans | L | 2-1 |
| Jamaïque - Premier League | 2019/03/03 20:30 | UWI Pelicans v Portmore United | L | 0-1 |
| Jamaïque - Premier League | 2019/01/13 20:00 | Portmore United v UWI Pelicans | W | 1-2 |
| Jamaïque - Premier League | 2018/10/28 20:00 | Portmore United v UWI Pelicans | D | 1-1 |
| Jamaïque - Premier League | 2018/02/25 20:00 | UWI Pelicans v Portmore United | W | 3-0 |
| Jamaïque - Premier League | 2017/12/28 20:00 | Portmore United v UWI Pelicans | L | 5-1 |
| Jamaïque - Premier League | 2017/11/01 20:00 | Portmore United v UWI Pelicans | W | 0-1 |
Home History
| Jamaïque - Premier League | 2020/03/02 00:00 | Waterhouse v UWI Pelicans | L | 3-1 |
| Jamaïque - Premier League | 2020/02/23 20:30 | UWI Pelicans v Cavalier | L | 0-3 |
| Jamaïque - Premier League | 2020/02/17 00:00 | Mount Pleasant FA v UWI Pelicans | L | 3-0 |
| Jamaïque - Premier League | 2020/01/30 20:00 | UWI Pelicans v Arnett Gardens | L | 1-3 |
| Jamaïque - Premier League | 2020/01/26 20:00 | UWI Pelicans v Molynes United FC | D | 1-1 |
| Jamaïque - Premier League | 2020/01/19 20:00 | Tivoli Gardens v UWI Pelicans | L | 1-0 |
| Jamaïque - Premier League | 2020/01/12 20:00 | UWI Pelicans v Dunbeholden FC | D | 0-0 |
| Jamaïque - Premier League | 2020/01/06 00:00 | Waterhouse v UWI Pelicans | D | 2-2 |
Away History
| Jamaïque - Premier League | 2020/03/05 20:00 | Portmore United v Harbour View FC | D | 0-0 |
| Jamaïque - Premier League | 2020/03/01 20:30 | Portmore United v Tivoli Gardens | L | 0-1 |
| Coupe des champions CONCACAF | 2020/02/26 03:15 | Cruz Azul v Portmore United | L | 4-0 |
| Coupe des champions CONCACAF | 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 |
| Jamaïque - Premier League | 2020/01/30 20:00 | Dunbeholden FC v Portmore United | W | 1-4 |
| Jamaïque - Premier League | 2020/01/26 20:00 | Portmore United v Vere United | W | 5-0 |