Cup Winners
| Season | Club | |
| 2022/2023 |  | Lion City Sailors |
| 2021/2022 |  | Hougang United |
| 2018/2019 |  | Tampines Rovers |
| 2017/2018 |  | Albirex Niigata Singapore |
| 2016/2017 | | Albirex Niigata Singapore |
| 2015/2016 | | Albirex Niigata Singapore |
| 2014/2015 | | Albirex Niigata Singapore |
| 2013/2014 |  | Balestier Khalsa |
| 2012/2013 | | Lion City Sailors |
| 2010/2011 | | Lion City Sailors |
| 2009/2010 |  | BG Pathum United |
| 2008/2009 |  | Geylang International |
| 2007/2008 |  | Warriors FC |
| 2006/2007 | | Warriors FC |