| 24.02.2025 |  PRE | Waterhouse FC Waterhouse FC | 1 - 0 | Portmore United Portmore United | | |
| 25.11.2024 | PRE | Portmore United Portmore United | 0 - 0 | Waterhouse FC Waterhouse FC | | |
| 11.03.2024 | PRE | Portmore United Portmore United | 0 - 0 | Waterhouse FC Waterhouse FC | | |
| 11.12.2023 | PRE | Waterhouse FC Waterhouse FC | 1 - 1 | Portmore United Portmore United | | |
| 01.05.2023 | PRE | Portmore United Portmore United | 1 - 1 | Waterhouse FC Waterhouse FC | | |
| 30.01.2023 | PRE | Waterhouse FC Waterhouse FC | 1 - 1 | Portmore United Portmore United | | |
| 26.04.2022 | PRE | Waterhouse FC Waterhouse FC | 3 - 0 | Portmore United Portmore United | | |
| 07.02.2022 | PRE | Portmore United Portmore United | 0 - 4 | Waterhouse FC Waterhouse FC | | |
| 10.09.2021 | PRE | Portmore United Portmore United | 0 - 1 | Waterhouse FC Waterhouse FC | | |
| 28.11.2019 | PRE | Waterhouse FC Waterhouse FC | 4 - 1 | Portmore United Portmore United | | |
| 11.11.2019 | PRE | Portmore United Portmore United | 1 - 1 | Waterhouse FC Waterhouse FC | | |
| 17.05.2019 |  CAR | Portmore United Portmore United | 1 - 1 | Waterhouse FC Waterhouse FC | | |
| 30.04.2019 | PRE | Portmore United Portmore United | 1 - 0 | Waterhouse FC Waterhouse FC | | |
| 15.03.2019 | PRE | Portmore United Portmore United | 0 - 0 | Waterhouse FC Waterhouse FC | | |
| 17.12.2018 | PRE | Waterhouse FC Waterhouse FC | 1 - 1 | Portmore United Portmore United | | |
| 09.11.2018 | PRE | Waterhouse FC Waterhouse FC | 2 - 2 | Portmore United Portmore United | | |
| 24.04.2018 | PRE | Portmore United Portmore United | 4 - 3 | Waterhouse FC Waterhouse FC | | |
| 02.03.2018 | PRE | Portmore United Portmore United | 0 - 1 | Waterhouse FC Waterhouse FC | | |
| 14.12.2017 | PRE | Portmore United Portmore United | 2 - 1 | Waterhouse FC Waterhouse FC | | |
| 16.10.2017 | PRE | Waterhouse FC Waterhouse FC | 0 - 5 | Portmore United Portmore United | | |
| 13.04.2017 | PRE | Waterhouse FC Waterhouse FC | 1 - 4 | Portmore United Portmore United | | |
| 19.12.2016 | PRE | Portmore United Portmore United | 0 - 0 | Waterhouse FC Waterhouse FC | | |
| 07.11.2016 | PRE | Portmore United Portmore United | 1 - 0 | Waterhouse FC Waterhouse FC | | |
| 28.03.2016 | PRE | Portmore United Portmore United | 1 - 0 | Waterhouse FC Waterhouse FC | | |
| 30.11.2015 | PRE | Portmore United Portmore United | 0 - 0 | Waterhouse FC Waterhouse FC | | |
| 21.09.2015 | PRE | Waterhouse FC Waterhouse FC | 1 - 2 | Portmore United Portmore United | | |
| 02.05.2014 | PRE | Portmore United Portmore United | 0 - 2 | Waterhouse FC Waterhouse FC | | |
| 21.02.2014 | PRE | Waterhouse FC Waterhouse FC | 1 - 0 | Portmore United Portmore United | | |
| 09.12.2013 | PRE | Portmore United Portmore United | 2 - 2 | Waterhouse FC Waterhouse FC | | |
| 15.04.2013 | PRE | Waterhouse FC Waterhouse FC | 3 - 0 | Portmore United Portmore United | | |
| 26.02.2013 | PRE | Portmore United Portmore United | 1 - 1 | Waterhouse FC Waterhouse FC | | |
| 26.11.2012 | PRE | Waterhouse FC Waterhouse FC | 1 - 0 | Portmore United Portmore United | | |
| 18.09.2012 | PRE | Portmore United Portmore United | 1 - 0 | Waterhouse FC Waterhouse FC | | |
| 07.05.2012 | PRE | Portmore United Portmore United | 1 - 1 | Waterhouse FC Waterhouse FC | | |
| 19.03.2012 | PRE | Waterhouse FC Waterhouse FC | 1 - 2 | Portmore United Portmore United | | |
| 05.01.2012 | PRE | Portmore United Portmore United | 1 - 0 | Waterhouse FC Waterhouse FC | | |
| 31.10.2011 | PRE | Waterhouse FC Waterhouse FC | 1 - 2 | Portmore United Portmore United | | |
| 21.03.2011 | PRE | Portmore United Portmore United | 0 - 1 | Waterhouse FC Waterhouse FC | | |
| 03.01.2011 | PRE | Waterhouse FC Waterhouse FC | 1 - 1 | Portmore United Portmore United | |
|