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2008 -
Carl “De Panman” Richards (/)
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2007 -
Keithroy “De Bear” Morson’s (“ I Say No” /“Support Party” )
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2006 -
Tyronne “Edimelo” Thomas (/)
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2005 -
Ivena “Queen Ivena” Phillip (/)
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2004 -
Ivena “Queen Ivena” Phillip (Reparation From Africa/After Lester)
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2003 -
Ivena “Queen Ivena” Phillip (Robin Hood/Agenda)
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2002 -
Lynwall “Zero” Joseph (Aids/I Am Sorry)
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2001 -
Trevor " Zacari" King (Fine Ants/Allergies)
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2000 -
Toriano "Onyan" Edwards (Criteria/Money)
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1999 -
Toriano "Onyan" Edwards (Family/Swim)
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1998 -
Toriano "Onyan" Edwards (Stand Up For Antigua/Ghetto Life)
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1997 -
Toriano "Onyan" Edwards (Crazy Man/Wile Out)
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1996 -
Davidson "Bankers" Benjamin (Me De Ras/Fire Go Bun Dem)
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1995 -
Ira "Smarty Jr." Harvey (Draw the Line/Follow the Leader)
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1994 -
Ira "Smarty Jr." Harvey (What Black Power Means/Cry for Change)
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1993 -
Ira "Smarty Jr." Harvey (Never Again/Role of the Calypsonians)
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1992 -
Mclean "Short Shirt" Emmanuel (Share the Honey/Last J'ouvert)
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1991 -
Trevor "Zacari" King (Jail Dem/Guilty of Being Black)
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1990 -
Lynwall "Zero" Joseph (Kneel in Prayer/Speculation)
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1989 -
Julian "Fiah" Lawrence (Faithful Nationals/Family Affair)
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1988 -
Mclean "Short Shirt" Emmanuel (Aids/Fire)
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1987 -
Mclean "Short Shirt" Emmanuel (Hari Kari/J'ouvert Rhythm)
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1986 -
Mclean "Short Shirt" Emmanuel (World in Distress/Jennifer)
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1985 -
Rupert "Swallow" Philo (All is not Lost/Tong Mash Dong)
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1984 -
Glenmore "Progress" Shepherd (Madness/You Getting It)
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1983 -
Paul "Obstinate" Richards (Antigua's True Heroes/Children Melee)
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1982 -
Paul "Obstinate" Richards (Coming to Talk to You/Elephant Walk)
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1981 -
Paul "Obstinate" Richards (Coming to Talk to You/Elephant Walk)
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1980 -
Mclean "Short Shirt" Emmanuel (Help/Summer Festival)
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1979 -
Mclean "Short Shirt" Emmanuel (Not by Might/Kangaroo Jam)
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1978 -
Rupert "Swallow" Philo (One Love, One Hope, One Destiny /Whinning)
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1977 -
Rupert "Swallow" Philo (Dawn of a New Day/Jam Dem Back)
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1976 -
Mclean "Short Shirt" Emmanuel (Inspite of All/Tourist Leggo)
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1975 -
Mclean "Short Shirt" Emmanuel (Awake/Cry for A Change)
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1974 -
Mclean "Short Shirt" Emmanuel (This Land/Lucinda)
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1973 -
Rupert "Swallow" Philo (March for Freedom/Push Ya Push Dey)
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1972 -
Mclean "Short Shirt" Emmanuel (Star Black/Pull Together)
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1971 -
Joseph "Calypso Joe" Hunte (Educate the Youths/Recorded in History)
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1970 -
Mclean "Short Shirt" Emmanuel (Black like me/Technical School)
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1969 -
Mclean "Short Shirt" Emmanuel (Heart Transplant /Carnival on the Moon)
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1968 -
Manroy "Creole" Hunte (Martin Luther King/Proud Antiguans)
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1967 -
Manroy "Creole" Hunte (Independence Carnival/Neighbour, Neighbour)
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1966 -
Mclean "Short Shirt" Emmanuel (Paradox of Life/They Scorning Me)
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1965 -
Mclean "Short Shirt" Emmanuel (Blessed (The Child That Has Its Own) /Beatles MBE)
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1964 -
Mclean "Short Shirt" Emmanuel (No Place Like Home/Heritage)
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1963 -
Kenneth "Tennyson" George (Racial Tension/Gagarin)
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1962 -
Eugene "Canary" Henry (Island People Names/Immigration Bill)
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1961 -
George "Zemakai" Edwards (Tribute to Radio Antigua/Fidel Castro)
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1960 -
Eugene "Canary" Henry (Slapping Hands/Gem of the Caribbean)
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1959 -
Fitzroy "Peculiar" Richards (Chemis/Shimmy)
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1958 -
Paul "Obstinate" Richards (Dance, Dance, Dance /Obsti Will Sing Again)
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1957 -
Samuel "Styler" Ryan (Water Wet Me Bed/Don't Back Back On Me)
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