Gundy and the University of Utah's Kyle Whittingham are currently the second-longest tenured FBS coaches with one school, trailing only Kirk Ferentz.

At Midwest City High School, Gundy played quarterback, and was voted Oklahoma Player of the Year in 1986.

After the 1996 season, Gundy moved again, this time to Maryland where he was wide receiver coach and passing game coordinator from 1997 to 2000 for the Terps.

In 2001, the Oklahoma State University head football coach job became vacant when Bob Simmons resigned and a search produced Les Miles and Mike Gundy as the finalists.

Gundy's first season saw the expulsion of eleven players from the team and the Cowboys struggled to a 4–7 record winning only one Big 12 conference game.

[7] The team featured two-time Biletnikoff Award winner Justin Blackmon and quarterback Brandon Weeden, both first-round draft picks in the 2012 NFL draft,[8] as well as a defense that led the FBS in turnover margin[9] The team also appeared in the program's first BCS game, defeating Andrew Luck and the Stanford Cardinal 41–38 in overtime at the 2012 Fiesta Bowl.

[12] On September 22, 2007, Gundy made comments that became the subject of a nationwide media controversy and generated a viral video.

During a press conference following his team's victory over the Texas Tech Red Raiders, Gundy criticized an article by Jenni Carlson of The Oklahoman.

[13][14][15] The article contained guesses as to why quarterback Bobby Reid, who had been publicly supported by the coaching staff earlier in the year, was demoted to second-string.

Gundy condemned the article as a personal attack on a young player and offered himself as a better target for criticism when he shouted "Come after me!

[18] Mike Griffith, president of the Football Writers Association of America, called Gundy's behavior "completely inappropriate".

"[20] Gundy would later state that the incident was a blessing in disguise, as the image of his strident defense of one of his players had a lasting positive effect on recruiting.

The allegations concerning Gundy included involvement in a bonus system for players along with direct payments and no-show or sham jobs involving boosters, continuing diminished academic standards including players playing who were otherwise academically ineligible such as having players' school work done by so-called tutors and other school personnel, tolerating widespread drug abuse among the players by continuing a sham drug counseling program and selective drug enforcement, and also purportedly like Miles, personally interviewing hostess candidates for the Orange Pride hostess program and facilitating some hostesses having sex with prospective recruits.

Following the SI series Oklahoma State conducted an intensive review of practices policies led by Charles Smart.

[27] Gundy subsequently issued an apology, saying he was "disgusted" by OAN's attitude towards the Black Lives Matter movement.

[28] In light of the controversy, Gundy suggested taking a $1M pay cut and agreed to other concessions concluding the incident.