Duke began his career with minor roles in theatre productions and recurring roles on the CBS science fiction series Person of Interest (2014–2015) and the ABC sitcom Modern Family (2016).
Winston Duke se narodil 15.11.1986 v Argyle. Herec pocházející z Trinidadu a Tobaga, žil s rodiči a sestrou Cindy od svých osmi let v newyorském Brooklynu.