- Demi-finaliste de la Gold Cup : 2000 -

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www.tnt.fifa.com

Année	Championnat	Coupe
1908	Clydesdale	-------
1909	Casuals	-------
1910	Shamrock	-------
1911	Shamrock	-------
1912	Casuals	-------
1913	Casuals	-------
1914	Casuals	-------
1915	Clydesdale	-------
1916	-------	-------
1917	-------	-------
1918	-------	-------
1919	Queen's Park	-------
1920	Royal Sussex	-------
1921	Casuals	-------
1922	Shamrock	-------
1923	Shamrock	-------
1924	Shamrock	-------
1925	Shamrock	-------
1926	Sporting Club	-------
1927	Maple FC	Shamrock
1928	Maple FC	Casuals
1929	Casuals	Everton
1930	Everton	Everton
1931	Everton	Everton
1932	Everton	Everton
1933	Queen's Royal College	-------
1934	Casuals	Casuals
1935	Casuals	Sporting Club
1936	Sporting Club	Shamrock
1937	Sporting Club	UBOT
1938	Casuals	West Ham
1939	Notre Dame SC	Casuals
1940	Casuals	Maple FC
1941	Casuals	UBOT
1942	Colts	Spitfire
1943	Fleet Air Arm	UBOT
1944	Shamrock	Colts
1945	Colts	Colts
1946	Notre Dame SC	Maple FC
1947	Colts	Notre Dame SC
1948	Malvern	Colts
1949	Malvern	Maple FC & Carlton
1950	Maple FC	UBOT
1951	Maple FC	UBOT & Providence
1952	Maple FC	Malvern
1953	Maple FC	Maple FC
1954	Sporting Club	UBOT
1955	Sporting Club	Malvern
1956	Notre Dame SC	TPD
1957	Colts	Shell & Shamrock
1958	Shamrock	Casuals
1959	Shamrock	Shamrock
1960	Maple FC	Malvern
1961	Maple FC	Malvern & Apex
1962	Maple FC	Dynamos
1963	Maple FC	Maple FC
1964	Paragon	Paragon
1965	Regiment	Malvern & BP Palo Seco
1966	Regiment	Regiment & Juniors
1967	Maple FC	Regiment
1968	Maple FC	Malvern
1969	Maple FC	Point Fortin
1970	Regiment	Maple FC
1971	-------	-------
1972	Defense Force	Maple FC
1973	Defense Force	-------
1974	Defense Force	Defense Force
1975	Defense Force	Police FC
1976	Defense Force	Falcons
1977	Defense Force	Malvern
1978	Defense Force	Falcons
1979	Police	-------
1980	Defense Force	-------
1981	Defense Force	Defense Force
1982	ASL Sports	ASL Sports
1983	ASL Sports	ASL Sports
1984	Defense Force	Motown United
1985	Defense Force	Defense Force
1986	Trintoc FC	Trintoc FC
1987	Defense Force	La Brea Angels
1988	Trintoc FC	Trintoc FC
1989	Defense Force	Defense Force
1990	Defense Force	Police FC
1991	Police	Defense Force
1992	Defense Force	Motown United
1993	Defense Force	Trintoc FC
1994	Police	Police FC
1995	Defense Force	United Petrotin
1996	Defense Force	Defense Force
1997	Defense Force	United Petrotin
1998	Joe Public	San Juan Jabloteh
1999	Defense Force	Williams Connection
2000	Williams Connection	Williams Connection
2001	Williams Connection	Joe Public
2002	San Juan Jabloteh	Williams Connection
2003	San Juan Jabloteh	North East Stars
2004	North East Stars	-------
2005	Williams Connection	San Juan Jabloteh
2006	Joe Public	WASA
2007	San Juan Jabloteh	Joe Public
2008	San Juan Jabloteh	Caledonia AIA
2009