He began his career appearing in a recurring role as Robert Foreman on the NBC sitcom The Cosby Show (1985–87), before playing Terrence Frye in the ABC Daytime soap opera, All My Children (1991–94).

He received three Daytime Emmy Award for Outstanding Younger Actor in a Drama Series nominations for his performance on All My Children.

Whitfield began his television career appearing in a recurring role on the NBC sitcom The Cosby Show as Robert Foreman (the love interest of Tempestt Bledsoe's character Vanessa Huxtable).

He has also appeared on The Jamie Foxx Show, NYPD Blue, Strong Medicine, Ghost Whisperer, CSI: Miami, Cold Case, and Grey's Anatomy.

[4] For his role as Remy Newell, he received a nomination for Outstanding Supporting Actor in a Drama Series at the 49th NAACP Image Awards.