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1904 - 1st Battalion Manchester Regiment
1905 - 1st Battalion Sherwood Foresters
1907 -
Singapore Cricket Club
1908 - 2nd Battalion West Kentshire Regiment
1909 - 3rd Battalion Middlesex Regiment
1910 -
3rd Battalion Middlesex Regiment
1911 - Singapore Cricket Club
1912 - Singapore Cricket Club
1913 -
Singapore Cricket Club
1914 - Singapore Cricket Club
1921 - 1st Battalion South Staffordshire
1922 -
2nd Battalion Middlesex Regiment
1923 - 2nd Battalion Middlesex Regiment
1924 - Singapore Cricket Club
1925 -
Singapore Chinese Football Association
1926 - 2nd Duke of Wellington's Regiment
1927 - 2nd Duke of Wellington's
Regiment
1928 - 2nd Duke of Wellington's Regiment
1929 - Singapore Cricket Club
1930 - Singapore Chinese
Football Association
1931 - Singapore Malays Football Association
1932 - Singapore Malays Football Association
1933 -
Singapore Malays Football Association
1934 - Singapore Chinese Football Association
1935 - Royal Engineers
1936 -
Royal Air Force
1937 - Singapore Chinese Football Association
1938 - Singapore Chinese Football Association
1939 -
Singapore Malays Football Association
1940 - Royal Air Force
1941 - Royal Air Force
1950 - Kota Raja
Club
1951 - Tiger Standard
1952 - Rovers Sport Club e Pasir Panjang Rovers
1953 - Tiger Standard
1954 -
Star Soccerites
1955 - Marine Department
1956 - Tiger Standard
1957 - Marine Department
1958 -
Darul Afiah
1959 - Darul Afiah
1960 - IRC
1975 - Geylang International
1976 - Geylang International
1977 -
Geylang International
1978 - Singapore Armed Forces
1979 - Tampines Rovers
1980 - Tampines Rovers
1981 -
Singapore Armed Forces
1982 - Farrer Park United
1983 - Tiong Bahru
1984 - Tampines Rovers
1985 -
Police
1986 - Singapore Armed Forces
1987 - Tiong Bahru
1988 - Geylang International
1989 -
Geylang International
1990 - Geylang International
1991 - Geylang International
1992 - Geylang International
1993 -
Geylang International
1994 - Perth Kangaroos
1996 - Geylang United
1997 - Singapore Armed Forces
1998 -
Singapore Armed Forces
1999 - Home United
2000 - Singapore Armed Forces
2001 - Geylang United
2002 -
Singapore Armed Forces
2003 - Home United
2004 - Tampines Rovers
2005 - Tampines Rovers
2006 -
Singapore Armed Forces
2007 - Singapore Armed Forces
2008 - Singapore Armed Forces
2009 - Singapore
Armed Forces
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