| Year | Given Names | Sobriquet | Venue | Song 1 | Song 2 |
|---|---|---|---|---|---|
| 1960 | Michael Wilkinson | Michael Wilkinson | Kensington Oval | Uh Coming Up | Nil |
| 1961 | Louis Sealy | Little Barron | Kensington Oval | Bachelors Beware | Nil |
| 1962 | Maurice Ashby | Mighty Producer | Kensington Oval | King Dyal | |
| 1963 | Don Marshall | Sir Don | Kensington Oval | 20th Century Husbands | Tax Dodgers |
| 1964 | Leopold Kirton | Mighty Charmer | Kensington Oval | Death Of Kennedy | |
| 1965 | Don Marshall | Sir Don | Kensington Oval | Granny's Proverbs | Dear Mary Bray |
| 1965 | Don Marshall | Sir Don | YMPC | The Offence | Dear Mary Bray |
| 1966 | No Competition | ||||
| 1967 | No Competition | ||||
| 1968 | Anthony Carter | Mighty Gabby | YMCA | Heart Transplant | |
| 1969 | Anthony Carter | Mighty Gabby | Globe Cinema | Family Planning | |
| 1970 | No Competition | ||||
| 1971 | No Competition | ||||
| 1972 | No Competition | ||||
| 1973 | Charles Smith | Mighty Romeo | YMPC | A Land So Dear | Pampalam |
| 1974 | Edrick Jordan | Mighty Dragon | Caribbean Pepperpot | Muhammad Ali | |
| 1975 | Don Marshall | Sir Don | Marine House, Ch.Ch | Tom Say | Make CARICOM Work |
| 1975 | Keith Christian | Mighty Destroyer | Culloden Farm / Culloden Rd. | Come Togother | |
| 1976 | Anthony Carter | Mighty Gabby | We Place / Barbarees Hill | Licks Like Fire | |
| 1976 | McDonald Blenman | Mighty Grynner | Culloden Farm / Culloden Rd. | Crop Over Bacchanal | |
| 1977 | No Competition | ||||
| 1978 | Keith Christian | Mighty Destroyer | National Stadium | I Man Bitter | Message To The People |
| 1979 | Victor Reid | Mighty Liar | National Stadium | She Want Pan | Nobody Don’t Like Me |
| 1980 | Anthony Blenman | Black Pawn | National Stadium | The Right To Criticise | Politician |
| 1981 | Charles Smith | Mighty Romeo | National Stadium | Gem Gone | Brother Fuzzy |
| 1982 | Stedson Wiltshire | Red Plastic Bag | National Stadium | Mr. Harding | Sugar Made Us Free |
| 1983 | Rained out | ||||
| 1984 | Stedson Wiltshire | Red Plastic Bag | National Stadium | Count The Cost | Bim |
| 1985 | Anthony Carter | Gabby | National Stadium | West Indian Politician | Culture |
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