5. Les Miles
The coach at Oklahoma State from 2001-04, Miles led the Cowboys to a 28-21 record and three bowl games during his tenure. The Cowboys went 1-2 in their bowl appearances. Miles’ conference win percentage was .500, going 16-16. Miles was 2-2 against OU, with one of those wins coming in Norman against the then-No. 4 Sooners in Miles first season. Miles was also an offensive coordinator under coach Bob Simmons at OSU before becoming the lead man.
4. Pappy Waldorf
The coach from 1929-33, Waldorf led the Cowboys to a 34-10-7 record, and still leads all Cowboys coaches in winning percentage at .735. Waldorf went 9-1 in conference games, and his teams won three conference championships. Waldorf is well known for making his players be hard workers and maintain discipline on the football field. Waldorf also coached at Oklahoma City University, Kansas State and Northwestern. Waldorf is the second-most successful coach in the modern era at UC Berkeley with 67 wins. He’s a member of the College Football Hall of Fame.
3. Jim Lookabaugh
Lookabaugh coached his OSU teams to a 58-41-7 record during his tenure from 1939 to 1949. Lookabaugh coached the only Cowboys football team to win a national championship in 1945. His teams won three conference championships and went 2-1 in bowl games, including a win in the 1945 Sugar Bowl. Lookabaugh is a member of the OSU Alumni Hall of Fame and the National Football Hall of Fame. He’s one of only three OSU coaches who played at OSU before pursuing a coaching career.
2. Pat Jones
Jones coached OSU 1984-94 and tallied a career 62-60-3 record. His teams won three bowl games, and Jones coached running back Barry Sanders, OSU’s only Heisman Trophy winner. He’s second all-time in games coached at OSU with 125. Jones was an assistant coach with the Cowboys before being hired as head coach. He also coached running back Thurman Thomas and quarterback Mike Gundy. Jones was a two-time Big 8 coach of the year and is a member of the College Football Hall of Fame.
1. Mike Gundy
The winningest coach in OSU history, Gundy has led the Cowboys to a 99-49 record during his time at the helm. He led the Cowboys to their only Big 12 championship in 2011. OSU beat then-No. 4 Stanford that seasin in theTostitos Fiesta Bowl. The Cowboys are 6-4 in bowl games under Gundy. Before he started his coaching career, Gundy played under Jones in the same backfield as Sanders and Thomas. He’s also coached 18 NFL Draft picks, including receiver Dez Bryant, offensive lineman Russell Okung, quarterback Brandon Weeden and defensive end Emmanuel Ogbah. Gundy also has a mullet better than the Boz could even dream of and will be aiming for his 100th win Saturday against West Virginia.