| Year | Winner | Album | Nominees | Ref. | 
  | 2003 | Sonia Collymore | "You Won't See Me Cry" | Gifted Man – Belinda Brady feat. Carla MarshallHeartache – Mr. Leroy BrownYou Won't See Me Cry – Sonia CollymoreShe Boom – Kulcha ConnectionTwo Hands Clapping – Snow
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  | 2004 | Leroy Brown | "Rent A Tile" | "Homie's Girl" – Carl Henry"Nana's Medley, Part 2" - Nana McLean"Smile" – Blessed"Tease Me" — Dezzie
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  | 2005 | Sonia Collymore | "WYSIWYG (What You See Is What You Get)" | Bare as She Dare – Carl Henry featuring Ce'CeileEmpty Barrel – Blessed featuring Kardinal OffishallIt's All Bless – KorexionUncorrupted – Steele
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  | 2006 | Blessed | "Reggae Time" | Hot Gal – Carl Henry feat. Rally BopLive Up – Truths and RightsMind & Body – Sold OdelRiver of Healing – Jah Beng
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  | 2007 | Korexion | "X-Rated" | Hard to See – HumbleIn the Streets – Trinity Chris feat. BlessedKulcha Connection – Kulcha ConnectionSurvival – Kwesi Selassie
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  | 2008 | Mikey Dangerous | "Don't Go Pretending" | "Don't Go" – Korexion"Final Road" – BlessedMusic Is My Life – Tanya MullingsTwo Chord Skankin' – Lyndon John X
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  | 2009 | Humble | "Everything" | "Jah Lift Me Up" – Blessed"Renegade Rocker" – Dubmatix"The Peacemaker’s Chauffeur" – Jason Wilson"Truth Will Reveal" – Souljah Fyah
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  | 2010 | Dubmatix feat. Prince Blanco | "Gonna Be Alright" | American Dream – Carl HenryBreaking Up – Tanya MullingsShow Me The Way – Kim DavisWha-La-La-Leng – Ghislain Poirier with Face-T
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  | 2011 | Elaine Lil'Bit Shepherd | "Likkle But Mi Tallawah" | Brighter Days – Lyndon John X"Don’t Wanna Go" – Tonya PMillion Chance – Tony AnthonySystem Shakedown – Dubmatix
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  | 2012 | Exco Levi | "Bleaching Shop" | "Lover's Paradise" – Jay Douglas"Seeds of Love & Life" – Dubmatix"Rescue Me" – Tanya Mullings"Woman" – Steele
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  | 2013 | Exco Levi | "Storms of Life" | "Radio" – Ammoye"Made for Love" – Melanie Durrant"Yours to Keep" – Makeshift InnocenceMove Ya’ – Elaine Lil'Bit Shepherd
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  | 2014 | Exco Levi | "Strive" | "Mandela" – Akustix"Baby It's You" – Ammoye"Love Collision" – Dru"Rebel Massive" – Dubmatix
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  | 2015 | Exco Levi | "Welcome the King" | "Love Inna Wi Heart" – Kirk Diamond feat. Bob da BuildaWake Up – Mikey DangerousHold On Till I Die – SteeleReal Talk – Tasha T
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  | 2016 | Kafinal feat. Daddy U Roy | "Nah Complain" | The French Sessions – Dubmatix"Hello Mama" – Exco Levi"Sexy Gal" – Kreesha Turner feat. T.O.K.Escape from the Mongoose Gang – Lyndon John X
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  | 2017 | Exco Levi | "Siren" | "Sorry" – Ammoye"Roll 'Dem" – Dubmatix feat. Gappy Ranks"Cry Every Day" – Blessed"Who Feels It Knows" – Jay Kartier
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  | 2018 | Kirk Diamond | "Greater" | The Light – Ammoye"Hold Up Slow Down" – Blessed"Neva Judge" – Eyesus"Love How You Whine" – K'Coneil feat. Kreesha Turner
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  | 2019 | Dubmatix | Sly & Robbie meet Dubmatix — Overdubbed | Money Don't Grow Pon Trees – BlessedGenesis – Chelsea StewartNarrative – Exco LeviTalk or No Talk – Kafinal feat. Queen Ifrica
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  | 2020 | Lyndon John X | The Warning Track | "Jah Children" – Jay Douglas"Wah Gwaan" – Exco Levi"Never Broken" – Petraa"Another Man" – Storry
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