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