S.League
| 2014 | Warriors FC | ||
| 2013 | Tampines Rovers FC | ||
| 2012 | Tampines Rovers FC | ||
| 2011 | Tampines Rovers FC | ||
| 2010 | Etoile FC | ||
| 2009 | Warriors FC | ||
| 2008 | Warriors FC | ||
| 2007 | Warriors FC | ||
| 2006 | Warriors FC | ||
| 2005 | Tampines Rovers FC | ||
| 2004 | Tampines Rovers FC | ||
| 2003 | Home United FC | ||
| 2002 | Warriors FC | ||
| 2001 | Geylang International | ||
| 2000 | Warriors FC | ||
| 1999 | Home United FC | ||
| 1998 | Warriors FC | ||
| 1997 | Warriors FC | ||
| 1996 | Geylang International |