Gruden began his coaching career as a graduate assistant at the University of Tennessee (1986-87). He then became an offensive assistant at Southeast Missouri State University (1988) and University of the Pacific, Stockton, Calif. (1989), before he joined the San Francisco 49ers (1990). In 1991 he was back at the college level at the University of Pittsburgh, Pa., but in 1992 the Green Bay Packers hired him as their wide receivers coach. In 1995 the Philadelphia Eagles made him their offensive coordinator, and in 1998 he took the Oakland Raiders' head coaching position. He guided the Raiders to division titles in 2000 and 2001, compiling a record of 40-28 in his first four years as a head coach.

The Buccaneers fired coach Tony Dungy in early 2002 and, in a move that raised more than a few eyebrows, obtained Gruden from the Raiders for $8 million and four draft picks. While Gruden was known for his offensive coaching ability, it was the fearsome Tampa Bay defense that had carried the team before he arrived, and the skilled motivator found ways to make the squad even better. The Buccaneers held opponents to fewer points (196) and fewer yards per game (252.8) than any other team in the league on the way to a 12-4 record and the National Football Conference (NFC) South division title and the Super Bowl victory. Gruden's last year as coach for Tampa Bay was 2008-2009 season. He then took a job with ESPN hosting Monday Night Football.