Whitfield began his television career appearing in the recurring role on the NBC sitcom The Cosby Show as Robert Foreman (the love interest of Tempestt Bledsoe's character Vanessa Huxtable). He later had a two year-run on The NBC daytime soap opera, Another World. From 1991 to 1994, Whitfield portrayed Terrence Frye in the ABC Daytime soap opera, All My Children. The role earned him nominations for three Daytime Emmy Award for Outstanding Younger Actor in a Drama Series and two Soap Opera Digest Awards.
After leaving daytime television, Whitfield starred in the short-lived Fox sitcom The Crew during 1995–96 season. In 1997, he went to star alongside Kadeem Hardison in another short-lived sitcom, Between Brothers. He had dramatic turn in the 2000 UPN series Secret Agent Man, it also was cancelled after one season. From 2002 to 2003, he starred alongside Tamara Taylor in another short-lived sitcom, Hidden Hills on NBC. From 2001 to 2002, Whitfield had a recurring role on the UPN sitcom Girlfriends. He also has appeared on The Jamie Foxx Show, NYPD Blue, Strong Medicine, Ghost Whisperer, CSI: Miami, Cold Case, and Grey's Anatomy.
In film, Whitfield has appeared opposite Vivica A. Fox in Two Can Play That Game (2001), The Salon (2004). He co-starred in White Man's Burden (1995), Mr. 3000 (2003), and Middle of Nowhere (2012). He has appeared along with his wife Salli Richardson in 2009 film Pastor Brown, and well as guest-starred on Eureka (in which he played Richardson's on-screen brother), and Stitchers. Whitfield also had the recurring roles on Make It or Break It and Mistresses as Rochelle Aytes' husband. In 2015, Whitfield joined the cast of BET reality comedy series Real Husbands of Hollywood.
In 2002, Whitfield married Actress Salli Richardson. They have two children: a daughter, Parker Richardson Whitfield, and a son, Dre Terrell Whitfield (born January 24, 2009).
In 2016, Whitfield was cast in the Oprah Winfrey Network drama series, Queen Sugar produced by Ava DuVernay and Oprah Winfrey.
