Calypso Monarchs 1960 - 2011
| Year | Stage Name | Name | Year | Stage Name | Name |
| 1960 | Young Sparrow | Douglas Duncan | 1986 | Man CP | Carlton Hall |
| 1961 | Young Wrangler | Jerome Ashton | 1987 | Black Ebou | Elgin Hamlett |
| 1962 | Caribbean Pete | Olsen Peters | 1988 | Poorsah | Cornelius Williams |
| 1963 | Caribbean Pete | Olsen Peters | 1989 | Papa Das | Anthony Glasgow |
| 1964 | Mighty Sheller | Jeffers Alexis | 1990 | Papa Das | Anthony Glasgow |
| 1965 | Mighty Sheller | Jeffers Alexis | 1991 | Poorsah | Cornelius Williams |
| 1966 | Mighty Leader | Selwyn Burke | 1992 | Rejector | Carlos Providence |
| 1967 | Mighty Sheller | Jeffers Alexis | 1993 | Black Ebou | Elgin Hamlett |
| 1968 | Mighty Ringo | Donald Ballantyne | 1994 | Vibrating Scakes | Kenneth Alleyne |
| 1969 | Lord Turkey | 1995 | Freedom Fighter | Angus Caine | |
| 1970 | Mighty Sheller | Jeffers Alexis | 1996 | ||
| 1971 | Mighty Sheller | Jeffers Alexis | 1997 | Sulle | Glenroy Caesar |
| 1972 | Mighty Sheller | Jeffers Alexis | 1998 | Man CP | Carlton Hall |
| 1973 | Mighty Sheller | Jeffers Alexis | 1999 | De Man Age | Errol Ballantyne |
| 1974 | Mighty Toiler | Quintyn Toby | 2000 | De Man Age | Errol Ballantyne |
| 1975 | Becket | Alston Cyrus | 2001 | Joy-C | Bridgette Creese |
| 1976 | Lord Hawk | Lloyd Providence | 2002 | Abijah | Elvis Abbey |
| 1977 | Mighty Toiler | Quintyn Toby | 2003 | Princess Monique | Monique Hector |
| 1978 | De Man Age | Errol Ballantyne | 2004 | Princess Monique | Monique Hector |
| 1979 | 2005 | Sulle | Glenroy Caesar | ||
| 1980 | Lord Have Mercy | Michael Ollivierre | 2006 | Ipa | Grantley Constance |
| 1981 | Professor | Reginal Cornwall | 2007 | Vibrating Scakes | Kenneth Alleyne |
| 1982 | Professor | Reginal Cornwall | 2008 | Princess Monique | Monique Hector |
| 1983 | Vibrating Scakes | Kenneth Alleyne | 2009 | Joy-C | Bridgette Creese |
| 1984 | Professor | Reginal Cornwall | 2010 | Joy-C | Bridgette Creese |
| 1985 | Man CP | Carlton Hall | 2011 | Tajoe | Maxwell Francis |