| Year | Manning Cup | Walker Cup | DaCosta Cup | Ben Francis Cup | Olivier Shield | FLOW Super Cup/ISSA Champions Cup |
| 1909 | Jamaica College | | | | Jamaica College | |
| 1910 | Jamaica College | | | | Jamaica College | |
| 1911 | no competition | | | | Munro College | |
| 1912 | St. George's College | | | | St. George's College | |
| 1913 | Jamaica College | | | | Jamaica College | |
| 1914 | Jamaica College | | | | Munro College | |
| 1915 | Jamaica College | | | | Jamaica College | |
| 1916 | Jamaica College | | | | Jamaica College | |
| 1917 | Jamaica College | | | | Jamaica College | |
| 1918 | Jamaica College | | | | Jamaica College | |
| 1919 | Jamaica College | | | | Jamaica College & Munro College | |
| 1920 | St. George's College | | | | St. George's College & Munro College | |
| 1921 | Jamaica College | | | | Jamaica College | |
| 1922 | Jamaica College | | | | Jamaica College | |
| 1923 | Wolmer's Boys | | | | Munro College | |
| 1924 | Wolmer's Boys | | | | Munro College | |
| 1925 | Wolmer's Boys | | | | Munro College | |
| 1926 | Wolmer's Boys | | | | Wolmer's Boys | |
| 1927 | St. George's College | | | | Munro College | |
| 1928 | St. George's College | | | | St. George's College | |
| 1929 | St. George's College | | | | Cornwall College | |
| 1930 | Wolmer's Boys | | | | Cornwall College | |
| 1931 | Wolmer's Boys | | | | Cornwall College | |
| 1932 | St. George's College | | | | Munro College | |
| 1933 | Jamaica College | | | | Munro College | |
| 1934 | Jamaica College | | | | Munro College | |
| 1935 | St. George's College | | | | St. George's College | |
| 1936 | St. George's College | | | | Munro College | |
| 1937 | St. George's College | | | | St. George's College | |
| 1938 | Wolmer's Boys | | | | Wolmer's Boys and Munro College | |
| 1939 | Wolmer's Boys | | | | Munro College | |
| 1940 | Jamaica College | | | | Cornwall College | |
| 1941 | Jamaica College | | | | Munro College | |
| 1942 | Jamaica College | | | | Jamaica College | |
| 1943 | Calabar High | | | | Munro College | |
| 1944 | no competition | | | | no competition | |
| 1945 | St. George's College | | | | Munro College | |
| 1946 | Jamaica College | | | | Jamaica College | |
| 1947 | St. George's College | | | | St. George's College | |
| 1948 | St. George's College | | | | St. George's College | |
| 1949 | Kingston College | | | | Kingston College | |
| 1950 | Kingston College | | Munro College | | Munro College | |
| 1951 | Kingston College | | Munro College | | Munro College | |
| 1952 | Kingston College | | Munro College | | Kingston College | |
| 1953 | Excelsior High School | | Cornwall College | | Cornwall College | |
| 1954 | no competition | | no competition | | no competition | |
| 1955 | St. George's College | | Cornwall College | | Cornwall College | |
| 1956 | St. George's College | | Cornwall College | | St. George's College | |
| 1957 | Kingston College | | Munro College | | Kingston College | |
| 1958 | Kingston College | | Cornwall College | | Cornwall College | |
| 1959 | St. George's College | | Cornwall College | | St. George's College & Cornwall College | |
| 1960 | no competition | | no competition | | no competition | |
| 1961 | Jamaica College | St. George's College | Munro College | | Jamaica College | |
| 1962 | Jamaica College | K.T.H.S. | Munro College | | Jamaica College | |
| 1963 | Jamaica College | Kingston College | Cornwall College | | Cornwall College | |
| 1964 | Kingston College | Kingston College | Munro College | | Kingston College | |
| 1965 | Kingston College | Kingston College | Vere Technical | | Kingston College | |
| 1966 | no competition | no competition | no competition | | no competition | |
| 1967 | Kingston College | Excelsior | Vere Technical | | Vere Technical | |
| 1968 | Jamaica College | Excelsior | Vere Technical | | Vere Technical | |
| 1969 | Excelsior | Trench Town | Vere Technical | | Vere Technical | |
| 1970 | Kingston College | Kingston College | Vere Technical | | Vere Technical | |
| 1971 | Wolmer's Boys | Wolmer's Boys | Vere Technical | | Wolmer's Boys | |
| 1972 | no competition | no competition | no competition | | no competition | |
| 1973 | no competition | no competition | no competition | | no competition | |
| 1974 | Jamaica College | Calabar High | ST.E.T.H.S. | | Jamaica College | |
| 1975 | Kingston College | Kingston College | Vere Technical | | Kingston College | |
| 1976 | Tivoli High | Wolmer's Boys | Vere Technical | | Vere Technical | |
| 1977 | Calabar High | Kingston College | Clarendon College | | Clarendon College | |
| 1978 | Camperdown High | Tivoli High | Clarendon College | | Clarendon College & Camperdown | |
| 1979 | Camperdown High | Excelsior | Dinthill | | Camperdown High | |
| 1980 | Excelsior | Excelsior | Vere Technical | | Vere Technical | |
| 1981 | Kingston College | K.T.H.S. | Dinthill | | Kingston College & Dinthill | |
| 1982 | Camperdown High | Camperdown High | Cornwall College | Vere Technical | Camperdown High | |
| 1983 | St. George's College | St. George's College | Cornwall College | Cornwall College | Cornwall College | |
| 1984 | St. George's College | St. George's College | Rusea's High | Cornwall College | St. George's College | |
| 1985 | Kingston College | St. George's College | Rusea's High | Rusea's High | Kingston College & Rusea's High | |
| 1986 | Kingston College | Meadowbrook | Herbert Morrison | St. Mary's College | Kingston College | |
| 1987 | ST.A.T.H.S. | Kingston College | Rusea's High | Rusea's High | ST.A.T.H.S. | |
| 1988 | Charlie Smith | Camperdown High | Herbert Morrison | Herbert Morrison | Charlie Smith | |
| 1989 | Excelsior | Meadowbrook | Rusea's High | Clarendon College | Rusea's High | |
| 1990 | Charlie Smith | Excelsior | Rusea's High | Clarendon College | Charlie Smith & Rusea's | |
| 1991 | Ardenne | St. George's College | Clarendon College | Cornwall College | Ardenne | |
| 1992 | St. George's College | St. George's College | Rusea's High | Rusea's High | Rusea's High | |
| 1993 | Excelsior High | St. George's College | Rusea's High | Glenmuir High | Excelsior High & Rusea's High | |
| 1994 | Wolmer's Boys | Tivoli High | Clarendon College | Glenmuir High | Wolmer's Boys | |
| 1995 | Charlie Smith | Charlie Smith | Cornwall College | Cornwall College | Charlie Smith | |
| 1996 | Norman Manley | Tivoli High | Clarendon College | Rusea's High | Norman Manley | |
| 1997 | no competition | no competition | no competition | no competition | no competition | |
| 1998 | Dunoon | Dunoon | Clarendon College | Clarendon College | Clarendon College & Dunoon | |
| 1999 | Tivoli High | Jonathan Grant | ST.E.T.H.S. | Glenmuir High | ST.E.T.H.S. | |
| 2000 | Norman Manley | Kingston College | Cornwall College | Cornwall College | Norman Manley | |
| 2001 | Bridgeport | Bridgeport | Cornwall College | Cornwall College | Cornwall College | |
| 2002 | Norman Manley | Charlie Smith | Rusea's High | Old Harbour | Rusea's High | |
| 2003 | Excelsior | St. Jago | Frome | Cornwall College | Excelsior & Frome | |
| 2004 | Excelsior | Excelsior | Glenmuir High | Glenmuir High | Glenmuir High | |
| 2005 | Calabar High | Tivoli High | Godfrey Stewart | Glenmuir High | Calabar High | |
| 2006 | Bridgeport | Eltham | Glenmuir High | Frome | Bridgeport & Glenmuir High | |
| 2007 | Jamaica College | Calabar High | Garvey Maceo High | Garvey Maceo High | Jamaica College | |
| 2008 | St. George's College | Excelsior | St. James High | St. James High | St. George's College | |
| 2009 | St. George's College | Jamaica College | ST.E.T.H.S. | Glenmuir High | St. George's College | |
| 2010 | Jamaica College | Jamaica College | Rusea's High | ST.E.T.H.S. | Jamaica College | |
| 2011 | St. George's College | St. George's College | Rusea's High | ST.E.T.H.S. | St. George's College | |
| 2012 | St. George's College | Wolmer's Boys | Glenmuir High | ST.E.T.H.S. | St. George's College | |
| 2013 | Jamaica College | Wolmer's Boys | ST.E.T.H.S. | ST.E.T.H.S. | Jamaica College | |
| 2014 | Jamaica College | St. George's College | Clarendon College | ST.E.T.H.S. | Jamaica College | Jamaica College |
| 2015 | Jamaica College | Wolmer's Boys | ST.E.T.H.S. | ST.E.T.H.S. | Jamaica College | St. George's College |
| 2016 | Jamaica College | Kingston College | Cornwall College | Lennon High | Jamaica College | Wolmer's Boys |
| 2017 | Jamaica College | Jamaica College | Rusea's High | Clarendon College | Jamaica College | Kingston College |
| 2018 | Kingston College | Hydel High | Clarendon College | Charlemont High | Clarendon College | Cornwall College |
| 2019 | Jamaica College | St. Catherine High | Clarendon College | B.B. Coke High | Clarendon College | Kingston College |
| 2020 | no competition | no competition | no competition | no competition | no competition | no competition |
| 2021 | Kingston College | St. Catherine High | Garvey Maceo High | Edwin Allen High | Kingston College | Clarendon College |
| 2022 | Jamaica College | Tivoli High | Clarendon College | Glemuir High | Clarendon College | Jamaica College |
| 2023 | Mona High | Jamaica College | Clarendon College | McGrath High | Clarendon College | Glenmuir High |
| 2024 | Kingston College | Mona High | Garvey Maceo High | ST.E.T.H.S. | Kingston College | Glenmuir High |
| 2025 | TBD | TBD | TBD | TBD | TBD | TBD |