Whitfield was drafted in the first round (eighth overall) of the 1992 NFL Draft by the Atlanta Falcons.[2] He played for the Falcons from 1992–2003 before he was released by the team. He then played for the Jacksonville Jaguars for the 2004 season. Whitfield, a 1999 Pro Bowler, was a fixture on the Falcons offensive line that finished 14‐2 in the regular season. The team went on to upset the Minnesota Vikings in the NFC Championship Game and advance to Super Bowl XXXIII. Whitfield attended Stanford University, where he was a consensus All-America student-athlete in his junior season. Although he made an early draft departure, Bob returned to the university to complete a Bachelors Degree of Arts in Economics in 2012. He was inducted in the Stanford Sports Hall of Fame in 2012.
Whitfield started for the New York Giants at left tackle during the 2006 season filling in after starter Luke Petitgout went down with injury. His time as a starter was marked by two episodes of him losing his cool and drawing costly personal fouls, twice on headbutts in key spots against the Dallas Cowboys and later in a week 16 loss against the New Orleans Saints. These actions lead to him receiving the nickname "Head-butt Bob" from many Giant fans as well as local columnists.[3][4] Due to these actions and general inconsistent play, Whitfield was benched for the final game of the season against the Washington Redskins and the subsequent playoff game against the Philadelphia Eagles.
On February 12, 2007, he announced his retirement on Sirius NFL radio.[5]
Whitfield also serves as a guest analyst for the UK's NFL Coverage on Sky Sports as well as contributing on local Atlanta television and radio.
On November 11, 2011, Whitfield was inducted into Stanford University's Hall of Fame[9][10] and in an interview, Whitfield admitted he was considering a return to his alma mater to complete his degree. Whitfield returned to Stanford in 2012 and received a degree in economics during a commencement ceremony held Father's Day with his kids present.[11]
Whitfield was married to The Real Housewives of Atlanta cast member Shereé Whitfield, with whom he has two children. The couple divorced in 2008. Sheree alleged that during their marriage Bob was abusive.[12]
He has a son, Kodi, who also played football at Stanford.[13]