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 |
| Jamaica - Premier League | 2019/03/14 20:30 | Portmore United v Waterhouse | D | 0-0 |
| Jamaica - Premier League | 2018/12/17 00:00 | Waterhouse v Portmore United | D | 1-1 |
| Jamaica - Premier League | 2018/11/09 00:00 | Waterhouse v Portmore United | D | 2-2 |
| Jamaica - Premier League | 2018/04/24 01:35 | Portmore United v Waterhouse | W | 4-3 |
| Jamaica - Premier League | 2018/03/01 20:30 | Portmore United v Waterhouse | L | 0-1 |
| Jamaica - Premier League | 2017/12/13 20:00 | Portmore United v Waterhouse | W | 2-1 |
| Jamaica - Premier League | 2017/10/15 20:30 | Waterhouse v Portmore United | W | 0-5 |
| Jamaica - Premier League | 2017/04/12 20:30 | Waterhouse v Portmore United | W | 1-4 |
| Jamaica - Premier League | 2016/12/18 20:00 | Portmore United v Waterhouse | D | 0-0 |
| Jamaica - Premier League | 2016/11/06 20:00 | Portmore United v Waterhouse | W | 1-0 |
| Jamaica - Premier League | 2016/03/27 20:30 | Portmore United v Waterhouse | W | 1-0 |
| Jamaica - Premier League | 2015/11/29 20:00 | Portmore United v Waterhouse | D | 0-0 |
| Jamaica - Premier League | 2015/09/20 21:00 | Waterhouse v Portmore United | W | 1-2 |