Past winners of Olivier Shield
1909 Jamaica College
1910 Jamaica College
1911 Munro College
1912 St George's College
1913 Jamaica College
1914 Munro College
1915 Jamaica College
1916 Jamaica College
1917 Jamaica College
1918 Jamaica College
1919 Jamaica College/Munro
1920 St George's/Munro College
1921 Jamaica College
1922 Jamaica College
1923 Munro College
1924 Munro College
1925 Munro College
1926 Wolmer's Boys'
1927 Munro College
1928 St George's College
1929 Cornwall College
1930 Cornwall College
1931 Cornwall College
1932 Munro College
1933 Munro College
1934 Munro College
1935 St George's College
1936 Munro College
1937 St George's College
1938 Wolmer's/Munro College
1939 Munro College
1940 Cornwall College
1941 Munro College
1942 Jamaica College
1943 Munro College
1944 No competition
1945 Munro College
1946 Jamaica College
1947 St George's College
1948 St George's College
1949 Kingston College
1950 Munro College
1951 Munro College
1952 Kingston College
1953 Cornwall College
1954 No competition
1955 Cornwall College
1956 St George's College
1957 Kingston College
1958 Cornwall College
1959 St George's/Cornwall College
1960 No competition
1961 Jamaica College
1962 Jamaica College
1963 Cornwall College
1964 Kingston College
1965 Kingston College
1966 No competition
1967 Vere Technical
1968 Vere Technical
1969 Vere Technical
1970 Vere Technical
1971 Wolmer's Boys'
1972 No competition
1973 No competition
1974 Jamaica College
1975 Kingston College
1976 Vere Technical
1977 Clarendon College
1978 Clarendon College
1979 Camperdown High
1980 Vere Technical
1981 Kingston College/Dinthill
1982 Camperdown High
1983 Cornwall College
1984 St George's College
1985 Kingston College/Rusea's
1986 Kingston College
1987 St Andrew Technical
1988 Charlie Smith High
1989 Rusea's High
1990 Rusea's/ Charlie Smith
1991 Ardenne High
1992 Rusea's High
1993 Excelsior/Rusea's
1994 Wolmer's Boys
1995 Charlie Smith High
1996 Norman Manley High
1997 No competition
1998 Clarendon/Dunoon Tech
1999 STETHS
2000 Norman Manley
2001 Cornwall College
2002 Rusea's High
2003 Excelsior High
2004 Glenmuir High
2005 Calabar High
2006 Bridgeport/Glenmuir
2007 Jamaica College
2008 St George's College
2009 St George's College
2010 Jamaica College
2011 St George's College
2012 St George's College
2013 Jamaica College
2014 Jamaica College