The oldest and most prestigious schoolboy football title; official name Sydney Olivier Interscholastic Challenge Shield; is currently played between winners of DaCosta Cup and Manning Cup.

 

1909-1919 1920-1930
1909 Jamaica College
1910 Jamaica College
1911 Potsdam College (Munro)
1912 St George’s College
1913 Jamaica College
1914 Potsdam College
1915 Jamaica College
1916 Jamaica College
1917 Jamaica College
1918 Jamaica College
1919 Jamaica College and Munro College
1920 St George’s College and 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
1931-1940 1941-1950
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 Boys and 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
1951-1960 1961-1970
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 Cornwall College and St George’s 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
1971-1980 1981-1990
1971 Wolmer’s Boys
1972 no competition
1973 no competition
1974 Jamaica College 4-0 STETHS
1975 Kingston College
1976 Camperdown and Vere Technical
1977 Clarendon College
1978 Clarendon College
1979 Camperdown
1980 Vere Technical
1981 Dinthill Technical
1982 Camperdown
1983 Cornwall College
1984 St George’s College 2-1 Jamaica College
1985 Rusea’s and Kingston College
1986 Kingston College
1987 St Andrew Technical
1988 Charlie Smith
1989 Rusea’s
1990 Rusea’s and Charlie Smith
1991-2000 2001-2010
1991 Ardenne
1992 Rusea’s
1993 Rusea’s and Excelsior
1994 Wolmer’s
1995 Charlie Smith
1996 Norman Manley
1997 No Competition
1998 Clarendon College & Dunoon Technical
1999 STETHS (St Elizabeth Technical High School)
2000 Norman Manley
2001 Cornwall College
2002 Rusea’s
2003 Excelsior
2004 Glenmuir High
2005 Calabar High 2-1 1-1 Godfrey Stewart High
2006 Bridgeport 1-1 n/p Glenmuir High [trophy shared]
2007 Jamaica College 2-0 Garvey Maceo High
2008 St George’s College 1-2 2-0 St James High
2009 St George’s College 3-2 2-1 STETHS
2010 Jamaica College 0-0 1-0 Rusea’s High
2011-
2011 St George’s College 1-0 1-0 Rusea’s High
2012 St. George’s College 4-1 1-1 Glenmuir
2013 Jamaica College 3-0 2-0 STETHS
2014 Jamaica College
2015 Jamaica College
2016 Jamaica College
2017 Jamaica College
2018 Clarendon College
2019 Clarendon College
2020 No Competition
2021 Kingston College 2-0 Garvey Maceo
2022 Clarendon College 3-0 Jamaica College
2023 Clarendon College 4-0 Mona