The National calypso Monarch competition is a yearly event that is held during the carnival season in Trinidad & Tobago. The competition is organised by The Trinbago Unified Calypsonians’ Organisation (TUCO).
| Year | Artists | Songs | Points |
| 2021 | No Competition due to Covid-19 | ||
| 2020 | Terri Lyons | Obeah Meghan My Dear | |
| 2019 | Ronaldo London | Man’s Imagination | |
| 2018 | Helon Francis | Change | |
| 2017 | Chalkdust | 75 Can’t Go In 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 Woe 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 | 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 Rhythm In Town Too Long | |
| 2004 | Chalkdust | Trinidad In The Cemetery Fish Mongrel | |
| 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 2000 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 | Good Driving Licensed Firearm | |
| De Lamo | 31 Years Old Trinity Is My Name | ||
| 1993 | Chalkdust | Misconception Kaiso In The Hospital | |
| 1992 | Mighty Sparrow | Both Of Them Survival | |
| 1991 | Black Stalin | Black Man Feeling 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 | I Thank Thee Her Majesty | |
| 1977 | Chalkdust | My Way Of Protest Shango Vision | |
| 1976 | Chalkdust | No Smut For Me Ah Put On Meh Guns Again | |
| 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 | |
| 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 & James Bomber’s Dream | |
| 1963 | Mighty Sparrow | Dan Is The Man In The Van | |
| 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 Suite Me | |
| 1957 | Lord Pretender | Que Sera Sera | |
| 1956 | Mighty Sparrow | Yankee’s Gone | |
| 1955 | Mighty Spoiler | Pick Sense Out Of Nonsense | |
| 1954 | Lord Melody | Second Spring | |
| 1953 | Mighty Spoiler | Bed Bug | |
| 1951 | Lord Melody | Jonah And The Bake | |
| 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 | |
| 1941 | Mighty Destroyer | Adolf Hitler | |
| 1940 | Roaring Lion | The Rise And Fall Of The British Empire | |
| 1939 | Growling Tiger | Trade Union |
