Cup Winners
| ฤดู | สโมสร | |
| 2013/2014 |  | Tampines Rovers |
| 2012/2013 | | Tampines Rovers |
| 2011/2012 | | Tampines Rovers |
| 2010/2011 | | Tampines Rovers |
| 2009/2010 |  | Warriors FC |
| 2007/2008 | | Warriors FC |
| ฤดู | สโมสร | |
| 2013/2014 | | Tampines Rovers |
| 2012/2013 | | Tampines Rovers |
| 2011/2012 | | Tampines Rovers |
| 2010/2011 | | Tampines Rovers |
| 2009/2010 | | Warriors FC |
| 2007/2008 | | Warriors FC |