| Monarch Wins | Calypsonian | Year | Tune #1 | Tune #2 |
| 9 | Chalkdust (Dr. Hollis Liverpool) | 1976 | Three Blind Mice | Ah Put on Me Guns |
| 1977 | Juba Dubai | Shango Vision |
| 1981 | Ah Can't Make | Things That Worry Me |
| 1989 | Chauffeur Wanted | Carnival is The Answer |
| 1993 | Kaiso in de Hospital | Misconceptions |
| 2004 | Trinidad in the Cemetary | Fish Mongrel |
| 2005 | AWhen I Vexed, I doh Rhyme | In Town Too Long |
| 2009 | My Heart and I | no second tune |
| 2017 | Learn From Arithmetic | no second tune |
| 8 | The Mighty Sparrow (Dr. Slinger Francisco) | 1956 | Jean and Dinah | no second tune |
| 1960 | Ten to One is Murder | Mae Mae |
| 1962 | Sparrow Come Back Home | Federation |
| 1963 | Dan is the Man | Kennedy |
| 1972 | Drunk and Disorderly | Rope |
| 1973 | School Days | Same Time, Same Place |
| 1974 | We Pass That Stage | Miss Mary |
| 1992 | Both of Them | Survival |
| 5 | Black Stalin (Dr. Leroy Calliste) | 1979 | Caribbean Man aka Caribbean Unity | Play One |
| 1985 | Isms SchismsWait | Dorothy |
| 1987 | Mr. Pan Maker | Burn Dem |
| 1991 | Bright Side | Black Man Feeling to Party |
| 1995 | In Times | .Sundar Popo |
| 4 | Cro Cro (Winston Rawlins)4 | 1988 | Three Bo Rats | Common Entrance Exam |
| 1990 | Political Dictionary | Party |
| 1996 | Dey Look for Dat | Support Commentary Calypso |
| 2007 | Nobody Ain’t Go Know | no second tune |
| Duke (Kelvin Pope) | 1968 | What is Calypso | Social Bacchanal |
| 1969 | Black is Beautiful | One Foot Visina |
| 1970 | Brotherhood of Man | See Through |
| 1971 | Mathematical Formula | Melvine & Yvonne |
| 2 | Chucky (Robert Gordon) | 2014 | Wah Yuh Think | Wedding Of De Century |
| 2015 | I Believe | The Rose |
| Luta (Morel Peters)1,3 | 1994 | Good Driving | Licenced Firearm |
| 2006 | Check The Foundation | Kaiso Kaiso |
| Singing Sandra (Sandra Des Vignes)2 | 1999 | Voices from the Ghetto | Song for Healing |
| 2003 | For Whom the Bell Tolls | Ancient Rhythm |
| The Mighty Spoiler (Theophilus Philip) | 1953 | Bed Bug | no second tune |
| 1955 | Pick Sense Out of Nonsense | no second tune |
| The Mighty Striker (Percy Oblington) | 1958 | Don't Blame the P.N.M | no second tune |
| 1959 | Ban the Hoola Hoop | Comparison |
| Sugar Aloes (Michael Osuna) | 2002 | Contribution | Jubilation |
| 2008 | Reflections | no second tune |
| 1 | Lord Melody (Fitzroy Alexander) | 1954 | Second Spring | no second tune |
| Lord Pretender (Aldric Farrell) | 1957 | Que Sera Sera | no second tune |
| Dougla (Clatis Ali) | 1961 | Lazy Man | Split Me in Two |
| The Mighty Bomber (Clifton Ryan) | 1964 | Joan and James | Bomber's Dream |
| Sniper (Mervyn Hodge) | 1965 | Portrait of Trinidad | More Production |
| The Mighty Terror (Fitzgerald Henry) | 1966 | Pan Jamboree | Last Year's Happiness |
| The Mighty Cypher aka Lord Cypher (Dillary Scott) | 1967 | Last Elections | If the Priest Could Play |
| Kitchener (Aldwyn Roberts) | 1975 | Tribute to Spree Simon | Fever |
| Calypso Rose (Mcartha Sandy-Lewis) | 1978 | Her Majesty | I Thank Thee |
| Lord Relator (Willard Harris) | 1980 | Food Prices | Take a Rest |
| Scrunter (Irwin Reyes Johnson) | 1982 | Lick-e-Thing | The Will |
| Tobago Crusoe (Othneil Bacchus) | 1983 | Don't Cry Now | South Africa |
| The Mighty Penguin (Sedley Joseph) | 1984 | We Living in Jail | Sorf Man |
| David Rudder | 1986 | The Hammer | Bahia Girl |
| Delamo (Franz Lambkin)1 | 1994 | 31 Years Old | Trinity is my Name |
| Gypsy (Winston Peters) | 1997 | Little Black Boy | Rhythm of the Nation |
| Mystic Prowler (Roy Lewis) | 1998 | Look Below The Surface | Vision of T&T in the Year 20 |
| The Mighty Shadow (Winston Bailey) | 2000 | What's wrong with Me | Scratch meh Back |
| Denyse Plummer | 2001 | Heroes | Nah Leaving |
| Kurt Allen | 2010 | Too Bright | no second tune |
| Karene Asche | 2011 | Careful What You Ask For | Uncle Jack |
| Duane O'Connor | 2012 | The Hunt is On | Long Live Calypso |
| Pink Panther (Eric Taylor) | 2013 | Travel Woe | Crying in the Chapel |
| Devon Seale | 2016 | Respect God's Voice | Spirit of Carnival |
| Helon Francis | 2017 | Change | no second tune |
| Ronaldo London | 2019 | Man’s Imagination | no second tune |
| Terri Lyons5 | 2020 | Obeah | Meghan My Dear |
notes:
1 - calypso monarch was a tied between Delamo and Luta.
2 - Singing Sandra, the first female too win the Calypso Monarch twice.
3 - Winner of the last Calypso Monarch to be held at the Queen's Park Savannah as it be demolish to make way for a new cultural center.
4 - 2007 TUCO gone back to the 1 song format for the calypso monarch instead of 2
calypso monarch competion from 1954 to present; 67 calypso monarch titles.
For 2011 TUCO had 1 song for the prelims and semi-finals and 2 songs for the finals!
5 - 2020 TUCO gone back too 2 songs for the finals!
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