Winners
- 1955/56 : Bermuda AA Wanderers 3-1 Southampton Rangers
- 1956/57 : PHC Zebras 4-3 Pembroke Juniors
- 1957/58 : Wellington Rovers 4-2 Bermuda AA Wanderers
- 1958/59 : Dock Hill Rangers 3-1 Devonshire Lions
- 1959/60 : PHC Zebras 5-3 Dock Hill Rangers
- 1960/61 : PHC Zebras 2-1 Young Men's Social Club
- 1961/62 : PHC Zebras 4-3 West End
- 1962/63 : Young Men's Social Club 3-1 Pembroke Juniors
- 1963/64 : Young Men's Social Club 3-1 Dock Hill Rangers
- 1964/65 : Young Men's Social Club 3-1 Dock Hill Rangers
- 1965/66 : Casuals 2-1 North Village
- 1966/67 : PHC Zebras 3-2 Devonshire Colts
- 1967/68 : Somerset Trojans 3-2 Devonshire Colts
- 1968/69 : Somerset Trojans 6-0 Southampton Rangers
- 1969/70 : Somerset Trojans 3-1 Academicals
- 1970/71 : PHC Zebras 1-0 Devonshire Colts
- 1971/72 : Somerset Trojans 0-0 2-2 4-1 PHC Zebras
- 1972/73 : Devonshire Colts 2-2 2-1 PHC Zebras
- 1973/74 : Devonshire Colts 3-0 WWC
- 1974/75 : PHC Zebras 3-1 Somerset Trojans
- 1975/76 : Somerset Trojans 2-1 Devonshire Colts
- 1976/77 : Somerset Trojans3-1 Southampton Rangers
- 1977/78 : North Village 3-1 PHC Zebras
- 1978/79 : Somerset Trojans 4-0 Devonshire Cougars
- 1979/80 : PHC Zebras 4-1 Warwick
- 1980/81 : Vasco da Gama FC 3-1 Somerset Trojans
- 1981/82 : Vasco da Gama FC 3-1 PHC Zebras
- 1982/83 : North Village 2-1 Vasco da Gama FC
- 1983/84 : Southampton Rangers 1-1 2-0 Devonshire Colts
- 1984/85 : Hotels International FC 2-1 PHC Zebras
- 1985/86 : North Village 2-0 Vasco da Gama FC
- 1986/87 : Dandy Town 2-2 1-0 PHC Zebras
- 1987/88 : Somerset Trojans 0-0 2-1 Devonshire Colts
- 1988/89 : North Village 2-1 PHC Zebras
- 1989/90 : Somerset Trojans 2-0 Dandy Town
- 1990/91 : Boulevard Blazers 1-1 2-0 PHC Zebras
- 1991/92 : PHC Zebras 2-1 Dandy Town
- 1992/93 : Boulevard Blazers 4-1 Devonshire Colts
- 1993/94 : Vasco da Gama FC 2-1 Dandy Town
- 1994/95 : Vasco da Gama FC 2-0 Devonshire Cougars
- 1995/96 : Boulevard Blazers 2-1 Southampton Rangers
- 1996/97 : Boulevard Blazers 3-2 (a.p.) Wolves
- 1997/98 : Vasco da Gama FC 2-1 (a.p.) Devonshire Colts
- 1998/99 : Devonshire Colts 1-0 Dandy Town
- 1999/00 : North Village 2-1 (a.p.) Devonshire Colts
- 2000/01 : Devonshire Colts 3-1 North Village
- 2001/02 : North Village 3-0 Dandy Town
- 2002/03 : North Village 5-1 Prospect
- 2003/04 : North Village 3-3 (a.p.) 2-1 (a.p.) (r.) Devonshire Cougars
- 2004/05 : North Village 2-0 Hamilton Parish FC
- 2005/06 : North Village 4-1 Dandy Town
- 2006/07 : Devonshire Colts 2-0 Boulevard Blazers (aet)
- 2007/08 : PHC Zebras 2-0 Dandy Town
- 2008/09 : Boulevard Blazers 5-3 Dandy Town
- 2009/10 : Devonshire Cougars
- 2010/11 : Devonshire Cougars 4-1 Southampton Rangers
- 2011/12 : Dandy Town 5-2 North Village
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Famous quotes containing the word winners:
“The two real political parties in America are the Winners and the Losers. The people dont acknowledge this. They claim membership in two imaginary parties, the Republicans and the Democrats, instead.”
—Kurt Vonnegut, Jr. (b. 1922)