Here is the list of all the Calypso Monarch winners, through out the years. ranging from 1957 to present.
| Year | Artist | Songs |
| 1957 | Samuel “Styler” Ryan | Water Wet Me Bed & Don’t Back Back On Me |
| 1958 | Paul “Obstinate” Richards | Dance Dance Dance & Obsti Will Sing Again |
| 1959 | Fitzroy “Peculiar” Richards | Chemis & Shimmy |
| 1960 | Eugene “Canary” Henry | Slapping Hands & Gem of the Caribbean |
| 1961 | George “Zemakai” Edwards | Tribute to Radio Antigua & Fidel Castro |
| 1962 | Eugene “Canary” Henry | Island People Names & Immigration Bill |
| 1963 | Kenneth “Tennyson” George | Racial Tension & Gagarin |
| 1964 | Mclean “Short Shirt” Emmanuel | No Place Like Home & Heritage |
| 1965 | Mclean “Short Shirt” Emmanuel | Blessed (The Child That Has Its Own) & Beatles MBE |
| 1966 | Mclean “Short Shirt” Emmanuel | Paradox of Life & They Scorning Me |
| 1967 | Manroy “Creole” Hunte | Independence Carnival & Neighbour Neighbour |
| 1968 | Manroy “Creole” Hunte | Martin Luther King & Proud Antiguans |
| 1969 | Mclean “Short Shirt” Emmanuel | Heart Transplant & Carnival on the Moon |
| 1970 | Mclean “Short Shirt” Emmanuel | Black Like Me & Technical School |
| 1971 | Joseph “Calypso Joe” Hunte | Educate the Youths & Recorded in History |
| 1972 | Mclean “Short Shirt” Emmanuel | Star Black & Pull Together |
| 1973 | Rupert “Swallow” Philo | March for Freedom & Push Ya Push Dey |
| 1974 | Mclean “Short Shirt” Emmanuel | This Land & Lucinda |
| 1975 | Mclean “Short Shirt” Emmanuel | Awake & Cry for A Change |
| 1976 | Mclean “Short Shirt” Emmanuel | Inspite of All & Tourist Leggo |
| 1977 | Rupert “Swallow” Philo | Dawn of a New Day & Jam Dem Back |
| 1978 | Rupert “Swallow” Philo | One Love One Hope One Destiny & Whinning |
| 1979 | Mclean “Short Shirt” Emmanuel | Not by Might & Kangaroo Jam |
| 1980 | Mclean “Short Shirt” Emmanuel | Help & Summer Festival |
| 1981 | Paul “Obstinate” Richards | Independence & Fat Man Dance |
| 1982 | Paul “Obstinate” Richards | Coming to Talk to You & Elephant Walk |
| 1983 | Paul “Obstinate” Richards | Antigua’s True Heroes & Children Melee |
| 1984 | Glenmore “Progress” Shepherd | Madness & You Getting It |
| 1985 | Rupert “Swallow” Philo | All is Not Lost & Tong Mash Dong |
| 1986 | Mclean “Short Shirt” Emmanuel | World in Distress & Jennifer |
| 1987 | Mclean “Short Shirt” Emmanuel | Hari Kari & J’ouvert Rhythm |
| 1988 | Mclean “Short Shirt” Emmanuel | Aids & Fire |
| 1989 | Julian “Fiah” Lawrence | Faithful Nationals & Family Affair |
| 1990 | Lynwall “Zero” Joseph | Kneel in Prayer & Speculation |
| 1991 | Trevor “Zacari” King | Jail Dem & Guilty of Being Black |
| 1992 | Mclean “Short Shirt” Emmanuel | Share the Honey & Last J’ouvert |
| 1993 | Ira “Smarty Jr.” Harvey | Never Again & Role of the Calypsonians |
| 1994 | Ira “Smarty Jr.” Harvey | What Black Power Means & Cry for Change |
| 1995 | Ira “Smarty Jr.” Harvey | Draw the Line & Follow the Leader |
| 1996 | Davidson “Bankers” Benjamin | Me De Ras & Fire Go Bun Dem |
| 1997 | Toriano “Onyan” Edwards | Crazy Man & Wile Out |
| 1998 | Toriano “Onyan” Edwards | Stand Up For Antigua & Ghetto Life |
| 1999 | Toriano “Onyan” Edwards | Family & Swim |
| 2000 | Toriano “Onyan” Edwards | Criteria & Money |
| 2001 | Trevor "Zacari" King | Fine Ants & Allergies |
| 2002 | Lynwall “Zero” Joseph | Aids & I am Sorry |
| 2003 | Lena “Ivena” Philip | Robin Hood & Agenda |
| 2004 | Lena “Ivena” Philip | Respiration for Africa – After Lester |
| 2005 | Lena “Ivena” Philip | Don’t Pressure Me & What Did Castro Tell You Mr. Spencer |
| 2006 | Tyrone “Edimelo” Thomas | That Was Yesterday & Rose |
| 2007 | Keithroy ‘De Bear’ Mason | Support Party |
| 2008 | Carl ‘De Pan Man’ Richards | De World Today - Not Me & De Politicks |
| 2009 | Trevor ‘Zacari’ King | It was for you Barack - Just a dream |
| 2010 | Keithroy ‘De Bear’ Mason | Leopard come home & Don’t Sing Bout De Judgment |
| 2011 | Keithroy ‘De Bear’ Mason | Melee for Sale & We get the change Ivena |
| 2012 | Keithroy ‘De Bear’ Mason | Time to Take our Place & Freedom for Mandela |
| 2013 | Tyrone “Eddie Mello” Thomas | Ghetto Boys & Light of Hope |
| 2014 | Thalia “Princess Thalia” King | Never Say Never & Heart and Soul |
| 2015 | Keithroy ‘De Bear’ Mason | Can’t Stop the Bear & Sing a Different Song |
| 2016 | Queen Thalia | My Guarantee & This Tenor Pan is Mine |
| 2017 | King Zacari | |
| 2018 | Queen Thalia | |
| 2019 |
