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| Season | 1st | 2nd |
|---|---|---|
| 2026 | – | |
| 2025-2026 | Mount Pleasant Academy | Montego Bay United |
| 2024-2025 | Mount Pleasant Academy | Arnett Gardens |
| 2023-2024 | Mount Pleasant Academy | Cavalier |
| 2022-2023 | Arnett Gardens | Cavalier |
| 2021 | Waterhouse | Dunbeholden |
| 2020 | Waterhouse | Cavalier |
| 2019-2020 | Waterhouse | Mount Pleasant Academy |
| 2018-2019 | – | |
| 2017-2018 | Portmore United | Arnett Gardens |
| 2016-2017 | Humble Lions | UWI |
| 2015-2016 | Portmore United | Arnett Gardens |
| 2014-2015 | Arnett Gardens | Waterhouse |
| 2013-2014 | Waterhouse | Harbour View |
| 2012-2013 | – | |
| 2011-2012 | – |