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1964 Young Men Social
1965 Young Men Social
1966 Young Men Social
1967 Somerset Cricket
1968 Somerset Cricket
1969 Somerset Cricket
1970 Somerset Cricket
1971 Pembroke Hamilton
1972 Devonshire Colts FC
1973 Devonshire Colts FC
1974 North Village Community
1975 Hotels International FC
1976 North Village Community
1977 Pembroke Hamilton
1978 North Village Community
1979 North Village Community
1980 Hotels International FC
1981 Southampton Rangers SC
1982 Somerset Cricket
1983 Somerset Cricket
1984 Somerset Cricket
1985 Pembroke Hamilton
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1986 Pembroke Hamilton
1987 Somerset Cricket
1988 Dandy Town SC
1989 Pembroke Hamilton
1990 Pembroke Hamilton
1991 Boulevard Community
1992 Pembroke Hamilton
1993 Somerset Cricket
1994 Dandy Town SC
1995 Boulevard Community
1996 Vasco da Gama FC
1997 Devonshire Colts FC
1998 Vasco da Gama FC
1999 Vasco da Gama FC
2000 PHC Zebras
2001 Dandy Town Hornets SC
2002 North Village Community
2003 North Village Community
2004 Dandy Town SC
2005 Devonshire Cougars
2006 North Village Community
2007 Devonshire Cougars
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