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| Season | 1st | 2nd |
|---|---|---|
| 2026-2027 | – | |
| 2025-2026 | Home United | Tampines Rovers |
| 2024-2025 | Home United | Tampines Rovers |
| 2023 | Albirex Niigata S | Home United |
| 2022 | Albirex Niigata S | Home United |
| 2021 | Home United | Albirex Niigata S |
| 2020 | Albirex Niigata S | Tampines Rovers |
| 2019 | DPMM FC Brunei | Tampines Rovers |
| 2018 | Albirex Niigata S | DPMM FC Brunei |
| 2017 | Albirex Niigata S | Tampines Rovers |
| 2016 | Albirex Niigata S | Tampines Rovers |