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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
