| 2026 |
Terri Lyons |
Blessings |
|
| 2025 |
Helon Francis |
To Whom it May Be |
|
| 2024 |
Machel Montano |
Soul of Calypso |
|
| 2023 |
Duane Ta'zyah O'Connor |
Sing Hallelujah |
|
| 2022 |
No competition (COVID-19) |
|
|
| 2021 |
No competition (COVID-19) |
|
|
| 2020 |
Terri Lyons |
Obeah / Meghan My Dear |
|
| 2019 |
Ronaldo London |
Imagination |
|
| 2018 |
Helon Francis |
Change |
|
| 2017 |
Chalkdust |
Learn From Arithmetic |
Ninth title. Also referred to by its lyric, 75 can't go into 14. |
| 2016 |
Devon Seale |
Respect God's Voice / Spirit of Carnival |
|
| 2015 |
Roderick "Chucky" Gordon |
The Rose / I Believe |
|
| 2014 |
Roderick "Chucky" Gordon |
Wey You Think / Wedding of de Century |
|
| 2013 |
Eric "Pink Panther" Taylor |
Travel Woes / Crying in the Chapel |
|
| 2012 |
Duane O'Connor |
The Hunt Is On / Long Live Calypso |
|
| 2011 |
Karene Asche |
Careful What You Ask For / Uncle Jack |
|
| 2010 |
Kurt Allen |
Too Bright |
|
| 2009 |
Chalkdust |
Ah Not In Dat / My Heart and I |
|
| 2008 |
Sugar Aloes |
Reflections |
|
| 2007 |
Cro Cro |
Nobody Ain't Go Know |
|
| 2006 |
Luta |
Check The Foundation / Kaiso Kaiso |
|
| 2005 |
Chalkdust |
A When I Vexed, I doh Rhyme / In Town Too Long |
|
| 2004 |
Chalkdust |
Trinidad in the Cemetery / Fish Mongrel |
Sources also cite Cro Cro for Sale. |
| 2003 |
Singing Sandra |
For Whom the Bell Tolls / Ancient Rhythm |
|
| 2002 |
Sugar Aloes |
Contribution / Jubilation |
|
| 2001 |
Denyse Plummer |
Heroes / Nah Leaving |
|
| 2000 |
Shadow |
What's Wrong with Me / Scratch meh Back |
|
| 1999 |
Singing Sandra |
Voices from the Ghetto / Song for Healing |
|
| 1998 |
Mystic Prowler |
Vision of T&T in the Year 2010 / Look Beneath the Surface |
|
| 1997 |
Gypsy |
Rhythm of a People / Little Black Boy |
|
| 1996 |
Cro Cro |
All Yuh Look for Dat / Deh Cyah Stop Social Commentary |
|
| 1995 |
Black Stalin |
In Time / Tribute to Sundar Popo |
|
| 1994 |
Luta & De Lamo (tie) |
Luta: Good Driving, Licensed Firearm. De Lamo: Trinity Is My Name, 31 Years Old |
Tie. |
| 1993 |
Chalkdust |
Misconception / Kaiso in the Hospital |
|
| 1992 |
Mighty Sparrow |
Both of Them / Survival |
|
| 1991 |
Black Stalin |
Ah Feel to Party / Look on the Bright Side |
|
| 1990 |
Cro Cro |
Political Dictionary / Party |
|
| 1989 |
Chalkdust |
Chauffeur Wanted / Carnival Is the Answer |
|
| 1988 |
Cro Cro |
Three Bo-rats / Corruption in Common Entrance |
|
| 1987 |
Black Stalin |
Mr Pan Maker / Burn Them |
|
| 1986 |
David Rudder |
The Hammer / Bahia Girl |
|
| 1985 |
Black Stalin |
Ism Schism / Wait Dorothy Wait |
|
| 1984 |
Penguin |
We Living in Jail / Sorf Man |
|
| 1983 |
Tobago Crusoe |
Don't Cry Now / South Africa |
|
| 1982 |
Scrunter |
The Will / Ah Lick E Thing |
|
| 1981 |
Chalkdust |
Things That Worry Me / I Can't Make |
|
| 1980 |
Lord Relator |
Food Prices / Take ah Rest Mr Prime Minister |
|
| 1979 |
Black Stalin |
Caribbean Man (Caribbean Unity) / Play One |
|
| 1978 |
Calypso Rose |
Her Majesty / I Thank Thee |
First woman to win; title renamed Calypso Monarch. |
| 1977 |
Chalkdust |
Shango Vision / My Way of Protest |
Sources also cite Juba Dubai. |
| 1976 |
Chalkdust |
Ah Put On Meh Guns Again / No Smut For Me |
Sources also cite Three Blind Mice. |
| 1975 |
Lord Kitchener |
Tribute to Spree Simon / Fever |
|
| 1974 |
Mighty Sparrow |
We Pass That Stage / Miss Mary |
|
| 1973 |
Mighty Sparrow |
School Days / Same Time, Same Place |
|
| 1972 |
Mighty Sparrow |
Drunk and Disorderly / Rope |
|
| 1971 |
Mighty Duke |
Mathematical Formula / Melvin & Yvonne |
|
| 1970 |
Mighty Duke |
Brotherhood of Man / See Through |
|
| 1969 |
Mighty Duke |
One Foot Visina / Black Is Beautiful |
|
| 1968 |
Mighty Duke |
What Is Calypso / Social Bacchanal |
|
| 1967 |
Mighty Cypher |
Last Elections / If the Priest Could Play |
|
| 1966 |
Mighty Terror |
Pan Jamboree / Last Year's Happiness |
|
| 1965 |
Sniper |
Portrait of Trinidad / More Production |
|
| 1964 |
Mighty Bomber |
Joan and James / Bomber's Dream |
|
| 1963 |
Mighty Sparrow |
Dan Is the Man in the Van / Kennedy |
|
| 1962 |
Mighty Sparrow |
Federation / Sparrow Come Back Home |
|
| 1961 |
Mighty Dougla |
Lazy Man / Split Me in Two |
|
| 1960 |
Mighty Sparrow |
Mae Mae / Ten to One Is Murder |
|
| 1959 |
Striker |
Ban the Hoola Hoop / Comparison |
|
| 1958 |
Striker |
Don't Blame the PNM / Can't Find a Job to Suit Me |
|
| 1957 |
Lord Pretender |
Que Sera Sera |
|
| 1956 |
Mighty Sparrow |
Jean and Dinah (Yankees Gone) |
First of eight titles. |
| 1955 |
Mighty Spoiler |
Pick Sense Out of Nonsense |
|
| 1954 |
Lord Melody |
Second Spring |
|
| 1953 |
Mighty Spoiler |
Bed Bug |
|
| 1952 |
No competition |
|
|
| 1951 |
Lord Melody |
Jonah and the Bake |
|
| 1950 |
No competition |
|
|
| 1949 |
Lord Melody |
Glory Mama Glory |
|
| 1948 |
Mighty Spoiler |
Royal Wedding |
|
| 1947 |
Atilla the Hun |
Million Dollar Jail |
|
| 1946 |
Atilla the Hun |
Daily Mail Report |
First title after the wartime break. |
| 1945 |
No Carnival (World War II) |
|
|
| 1944 |
No Carnival (World War II) |
|
|
| 1943 |
No Carnival (World War II) |
|
|
| 1942 |
No Carnival (World War II) |
|
|
| 1941 |
Mighty Destroyer |
Adolf Hitler |
|
| 1940 |
Roaring Lion |
Rise and Fall of the British Empire |
|
| 1939 |
Growling Tiger |
Trade Union |
|
