| 13.03.2025 |  PRE | Portmore United Portmore United | 1 - 0 | Mount Pleasant Mount Pleasant | | |
| 23.12.2024 | PRE | Mount Pleasant Mount Pleasant | 1 - 0 | Portmore United Portmore United | | |
| 16.09.2024 | PRE | Portmore United Portmore United | 0 - 2 | Mount Pleasant Mount Pleasant | | |
| 18.01.2024 | PRE | Portmore United Portmore United | 1 - 1 | Mount Pleasant Mount Pleasant | | |
| 23.10.2023 | PRE | Mount Pleasant Mount Pleasant | 1 - 0 | Portmore United Portmore United | | |
| 07.04.2023 | PRE | Portmore United Portmore United | 0 - 0 | Mount Pleasant Mount Pleasant | | |
| 22.11.2022 | PRE | Mount Pleasant Mount Pleasant | 0 - 0 | Portmore United Portmore United | | |
| 13.06.2022 | PRE | Portmore United Portmore United | 1 - 2 | Mount Pleasant Mount Pleasant | | |
| 28.03.2022 | PRE | Mount Pleasant Mount Pleasant | 0 - 2 | Portmore United Portmore United | | |
| 09.08.2021 | PRE | Portmore United Portmore United | 0 - 1 | Mount Pleasant Mount Pleasant | | |
| 25.11.2019 | PRE | Portmore United Portmore United | 2 - 0 | Mount Pleasant Mount Pleasant | | |
| 31.10.2019 | PRE | Portmore United Portmore United | 0 - 2 | Mount Pleasant Mount Pleasant | | |
| 16.04.2019 | PRE | Portmore United Portmore United | 1 - 1 | Mount Pleasant Mount Pleasant | | |
| 09.04.2019 | PRE | Mount Pleasant Mount Pleasant | 1 - 2 | Portmore United Portmore United | | |
| 21.01.2019 | PRE | Mount Pleasant Mount Pleasant | 1 - 1 | Portmore United Portmore United | | |
| 07.01.2019 | PRE | Portmore United Portmore United | 1 - 0 | Mount Pleasant Mount Pleasant | | |
| 17.09.2018 | PRE | Portmore United Portmore United | 1 - 2 | Mount Pleasant Mount Pleasant | |
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