Duke was born in Tobago, Trinidad & Tobago and moved to the U.S. with his mother, Cora Pantin, and sister when he was nine years old. He graduated from Brighton High School in Rochester, New York in 2004.
He started acting in theater productions for Portland Stage Company and Yale Repertory Theatre before being cast in Person of Interest. At Yale, he befriended fellow actor Lupita Nyong'o, with whom he would later star in Black Panther. Winston returned to his native Trinidad & Tobago in 2012 for the theatre production of An Echo in the Bone starring alongside actress Taromi Lourdes Joseph and directed by fellow Yale alumna Timmia Hearn Feldman.
|2018||Black Panther||M'Baku||Ryan Coogler||Nominated – MTV Movie Award for Best Fight|
|Avengers: Infinity War||Anthony & Joe Russo|
|2019||Us||Gabriel "Gabe" Wilson||Jordan Peele||Post-production|
|Avengers: Endgame||M'Baku||Anthony & Joe Russo||Post-production|
|2014||Law & Order: Special Victims Unit||Cedric Jones||Episode: "Gridiron Soldier"|
|2014–2015||Person of Interest||Dominic Besson / Mini||7 episodes|
|2015||The Messengers||Zahir Zakaria||3 episodes|
|Major Crimes||Curtis Turner||Episode: "#FindKaylaWeber"|
|2016||Modern Family||Dwight||3 episodes|