Head to Head
| Jamaica - Premier League | 2023/01/29 21:00 | Waterhouse v Portmore United | D | 1-1 |
| Jamaica - Premier League | 2022/04/26 00:30 | Waterhouse v Portmore United | L | 3-0 |
| Jamaica - Premier League | 2022/02/06 18:00 | Portmore United v Waterhouse | L | 0-4 |
| Jamaica - Premier League | 2021/09/10 15:00 | Portmore United v Waterhouse | L | 0-1 |
| Jamaica - Premier League | 2019/11/28 01:00 | Waterhouse v Portmore United | L | 4-1 |
| Jamaica - Premier League | 2019/11/10 20:00 | Portmore United v Waterhouse | D | 1-1 |
| Campeonato de Clubes da CFU | 2019/05/17 01:00 | Portmore United v Waterhouse | D | 1-1 |
| Jamaica - Play-Offs | 2019/04/30 01:35 | Portmore United v Waterhouse | W | 1-0 |
Home History
| Jamaica - Premier League | 2023/04/23 21:00 | Portmore United v Humble Lions | D | 1-1 |
| Taça da Jamaica | 2023/04/20 21:00 | Molynes United FC v Portmore United | D | 2-2 |
| Jamaica - Premier League | 2023/04/16 20:00 | Cavalier v Portmore United | L | 2-0 |
| Jamaica - Premier League | 2023/04/09 21:00 | Portmore United v Tivoli Gardens | W | 2-1 |
| Jamaica - Premier League | 2023/04/06 21:00 | Portmore United v Mount Pleasant FA | D | 0-0 |
| Jamaica - Premier League | 2023/04/02 22:30 | Harbour View FC v Portmore United | W | 0-1 |
| Jamaica - Premier League | 2023/03/26 21:00 | Portmore United v Faulkland FC | W | 4-0 |
| Jamaica - Premier League | 2023/03/19 22:30 | Dunbeholden FC v Portmore United | W | 1-3 |
Away History
| Jamaica - Premier League | 2023/04/23 21:15 | Waterhouse v Cavalier | W | 1-0 |
| Jamaica - Premier League | 2023/04/18 00:30 | Tivoli Gardens v Waterhouse | W | 0-1 |
| Jamaica - Premier League | 2023/04/09 21:15 | Waterhouse v Harbour View FC | L | 0-2 |
| Jamaica - Premier League | 2023/04/03 22:00 | Faulkland FC v Waterhouse | W | 2-3 |
| Jamaica - Premier League | 2023/03/28 00:30 | Waterhouse v Dunbeholden FC | D | 0-0 |
| Jamaica - Premier League | 2023/03/19 21:00 | Waterhouse v Mount Pleasant FA | W | 2-0 |
| Jamaica - Premier League | 2023/03/12 21:00 | Waterhouse v Chapelton Maroons FC | W | 3-2 |
| Jamaica - Premier League | 2023/03/05 21:00 | Waterhouse v Vere United | W | 2-1 |