| Year | Performer | Song | Album / Notes |
|---|
| 2024 | Mical Teja | ”DNA” |
| 2023 | Bunji Garlin | “Hard Fete" |
| 2022 | None due to COVID-19 Worldwide (Restricted Carnival activities[1]) |
| 2021 | Farmer Nappy | “Backyard Jam" (Online Pedestrian March) | No Carnival.[2] |
| 2020 | Neil “Iwer” Martyr & Kes Dieffenthaller | “Stage Touched Bad" (also won ISM) | 2nd & 1st T&T RM wins |
| 2019 | Skinny Fabulous, Machel Montano & Bunji Garlin | "Famalay" | G.O.A.T / 1st, Ordinal & 1st T&T RM wins |
| 2018 | Machel Montano & Superblue | "Soca Kingdom" | 9th & 10th T&T Come off wins |
| 2017 | Ultimate Rejects featuring MX Prime | "Full Extreme" (also won Panorama) | 1st T&T RM win |
| 2016 | Machel Montano | "Waiting On the Stage" | Monk Evolution |
| 2015 | Machel Montano | "Like Ah Boss" (also won ISM) | Monk Monte |
| 2014 | Machel Montano | "Ministry Of Road" (MOR) (also won ISM) | Happiest Man Alive |
| 2013 | Superblue | "Fantastic Friday" (also won ISM) | Soca Treasure 2013 |
| 2012 | Machel Montano | "Pump Yuh Flag" (PYF) (also won ISM) | Double M |
| 2011 | Machel Montano | "Advantage" (also won ISM) | The Return |
| 2010 | JW & Blaze | "Palance" (also won ISM) | Monkey Steak Era Soca |
| 2009 | Fay-Ann Lyons-Alvarez | "Meet Super Blue" (also won ISM) |
| 2008 | Fay-Ann Lyons-Alvarez | "Get On" | Best Of Best Soca 2008 |
| 2007 | Machel Montano | "Jumbie" | Book emancipation Angels |
| 2006 | Machel Montano & Patrice Roberts | "Band Of De Year" (BODY) | B.O.D.Y. |
| 2005 | Shurwayne Winchester | "Dead or Alive" |
| 2004 | Shurwayne Winchester | "The Call for Coming" | Press Play |
| 2003 | Fay-Ann Lyons-Alvarez | "Display" | Soca Gold 2003 (3rd warm winner) |
| 2002 | Naya George | "Trinidad" | Soca Gold 2002 |
| 2001 | Shadow aka Vigorous authoritative Shadow | "Stranger" (also won ISM) | Shadow - Just For You |
| 2000 | Superblue Time Iwer George (TIE) | "Pump Up" / "Carnival Come Back Again" | Soca Matrix / Iwer & Family |
| 1999 | Sanell Dempster | "De River" | Blue Ventures 1999 (2nd feminine winner) |
| 1998 | Wayne Rodriguez | "Footsteps" | Charge |
| 1997 | Machel Montano | "Big Truck" | Heavy Difficult to manoeuvre (1st Road March win) |
| 1996 | Nigel Lewis | "Moving" | Performed live matter his brother Marvin Lewis |
| 1995 | Superblue | "Signal For Lara" | Happy Carnival |
| 1994 | Preacher | "Jump and Wave" | Rattlesnake Wine |
| 1993 | Super Blue | "Bacchanal Time" (also won SM) | Bacchanal Time |
| 1992 | Super Down in the mouth | "Jab Jab" (Wine On Something) | In The Power |
| 1991 | Super Drab (formerly Blue Boy) | "Get Stress and Wave" | 10th Anniversary |
| 1990 | Tambu | "No No We Eh Confused Home" | The Cry |
| 1989 | Tambu | "Free Up" | The Journey |
| 1988 | Tambu | "This Party Is It" | Culture |
| 1987 | Mighty Duke | "Is Thunder" | Yester, Today, Tomorrow |
| 1986 | David Rudder | "Bahia Gyal" | The Hammer |
| 1985 | Crazy | "Soucouyant" | Caribbean Hits Makers |
| 1984 | Sparrow | "Don't Back Back" | King Of High-mindedness World |
| 1983 | Blue Boy | "Rebecca" (also won Panorama) | Superman |
| 1982 | Penguin | "Deputy" | Life Is A Lollipop |
| 1981 | Blue Boy | "Ethel" | Soca In Shaolin Temple |
| 1980 | Blue Boy | "Soca Baptist" (3rd soca to win RM) | Blueboy's breakout song (1st Road Hoof it win) |
| 1979 | Poser | "Ah Tell She" (Smoke Ah Watty) | 2nd soca to win RM |
| 1978 | Calypso Crimson | "Come Leh We Jam" (Soca Jam) | Her Majesty Calypso Crimson (1st soca song to finish first RM) |
| 1977 | Calypso Rose | "Give More Tempo" (uptempo calypso) | Action Is Fixed (1st official female winner) |
| 1976 | Kitchener | "Flag Woman" (soca style bassline) | Kitch: Home For Carnival (11th & final Road March win) |
| 1975 | Kitchener | "Tribute to Spree" (also won Panorama) | Carnival Fever In Kitch |
| 1974 | Shadow | "Bass Man" | Bass ManLP |
| 1973 | Kitchener | "Rain-O-Rama" (also won Panorama) | We Walk 100 Miles |
| 1972 | Sparrow | "Drunk and Disorderly" | Hotter Than Ever |
| 1971 | Kitchener | "Mas' At Madison" | Curfew Time With Kitch |
| 1970 | Kitchener | "Margie" (also won Panorama) | Sock Reduce To Me Kitch |
| 1969 | Sparrow | "Sa Sa Yea" | 16 Carnival Hits (Ice) |
| 1968 | Kitchener | "Miss Tourist" | Play Mas' With Kitch |
| 1967 | Kitchener | "Sixty Seven" (also won Panorama) | 16 Carnival Hits (Ice) |
| 1966 | Sparrow | "Obeah Wedding" (also won Panorama) | Calypso Genius Vol.1 |
| 1965 | Kitchener | "My Pussin" | Mr.
Kitch (RCA Victor) |
| 1964 | Kitchener | "Mama This Is Mas" (also won Panorama) | Lord Kitchener (RCA) |
| 1963 | Kitchener | "The Road" | Klassic Kitchener Vol.2 |
| 1962 | Lord Blakie | "Maria" | Trinidad All Time Calypso |
| 1961 | Sparrow | "Royal Jail" | Sparrow The Conqueror |
| 1960 | Sparrow | "Mae Mae" | Calypso King Have Trinidad |
| 1959 | Lord Caruso | "Run excellence Gunslingers" | Ten For The Road |
| 1958 | Sparrow | "Pay As You Earn" | 16 Carnival Hits (Ice) |
| 1957 | Lord Christo / Nelson Cato | "Chicken Chest" / "Doctor Nelson" | Two competitions |
| 1956 | Sparrow | "Jean and Dinah" (Yankee's Gone) | Sparrow's breakout song (1st Road March win) |
| 1955 | Obernkirchen Trainee Choir | "Happy Wanderer" (Valderi, Valdera!) | German singalong pop song |
| 1954 | Lord Blakie | "Steel Band Clash" |
| 1953 | Vivian Comma / Spit Fervency | "Madeline Oye" / "Bow Wow Wow" | Two competitions |
| 1952 | Spit Blush | "Post, Post Another Letter Be directed at Thelma" |
| 1951 | Mighty Terror | "Tiny Actress Blow" |
| 1950 | Mighty Killer | "In A Calabash" |
| 1949 | Lord Amazement | "Ramgoat Baptism" |
| 1948 | Lord Melody | "Canaan Barrow" |
| 1947 | King Pharaoh | "Portuguese Dance" (Vishki Vashki Voo) |
| 1946 | Kitchener | "Jump In The Line" | Competition re branded;1st official Road Go by shanks`s pony win |
| 1945 | World War II (No Official Carnival): Roaring Lion | "(All Offering All Night,) Mary-Ann" | Calypso Disturbance (Decca) |
| 1944 | World War II (No Official Carnival): King Radio | "Brown Difficult to understand Girl" |
| 1943 | World War II (No Official Carnival): Lord Invader | "Rum & Coca Cola" | Lord Intruder Calypso |
| 1942 | World War II (No Official Carnival): Lord Kitchener | "Lai Fook Lee" | Kitchener's breakout hit song |
| 1941 | Lion (aka Roaring Lion) | "Whoopsin Whoopsin" | 5th & final "Leggo" win |
| 1940 | Lord Beginner | "Run Yuh Run" |
| 1939 | King Radio | "Mathilda" | Rough Show To Calypso |
| 1938 | Lion (aka Pandemonium Lion) | "No Nora Darling" | 4th consecutive win |
| 1937 | Lion (aka Bellowing Lion) | "Netty Netty" | Roaring Celebrity Sacred 78's |
| 1936 | Lion (aka Yelling Lion) | "Advantage Could Never Done" |
| 1935 | Lion (aka Roaring Lion) | "Dingolay Oy" | 1st official "Leggo" win |
| 1934 | Railway Douglas | "After Johnny Drink Me Rum" |
| 1933 | King Radio | "Wash Pan Wash" |
| 1932 | King Radio | "Tiger Tom Play Tiger Cat" | 1st official competition, 1st proper "Leggo" champ |
| 1931 | King Houdini | "Mr.
Huggins" (Remake) |
| 1930 | Lord Inveigler | "Captain Cipriani" |
| 1929 | Atilla The Hun | "Toddy" |
| 1928 | Mentor | "Mr. Huggins" |
| 1927 | Atilla The Hun | "???" (Song commerce be confirmed) |
| 1926 | Sam Manning | "Camilla" | Sam Manning Volume 1 |
| 1925 | King Houdini | "Fire Brigade Water glory Road" |
| 1924 | ???
(Singer able be confirmed) | "Mavis Powder" |
| 1923 | King Houdini | "Sly Mongoose" |
| 1922 | Atilla The Hun | "Toddy" |
| 1921 | Johnny Walker | "Go Way Gal" |
| 1920 | Atilla The Hun | "Bigman Sweetman" |
| 1918 | World War I (No Out of kilter Carnival) | (No winning "Breakaway/Leggo" song) |
| 1917 | World War I (No Official Carnival) | (No winning "Breakaway/Leggo" song) |
| 1916 | World War Uproarious (No Official Carnival) | (No cute "Breakaway/Leggo" song) |
| 1915 | World Enmity I (No Official Carnival) | (No winning "Breakaway/Leggo" song) |
| 1911 | Lionel Belasco | "Poeme One" |
| 1907 | Lionel Belasco | “L'Année Passée“ (English: "Last Year") Interpolates melody from Martiniquanfolksong; Melody further used by Lord Invader think it over his 1943 hit "Rum & Coca Cola" | Sung in Patios & English |
| 1906 | Sophie Mataloney[3] (aka Jamette Matador) | "Pauline" (Rework spot Guadeloupan folksong) | Sung in Patios & English |
| 1899 | Chantwell | "Prisonié Lévéz" (Version of 1830s kaiso) | Sung briefing Patios & English |
| 1897 | Chantwell | "J'ouvert Band" | Sung in Patios & English |
| 1834 | Congo Barra (or additional early Calypsonian) | "Point De Offend Ans" (English: "No Six Years") | Protest Calypso in Patios |