The Oklahoma State Cowboys football program is a college football team that represents Oklahoma State University–Stillwater. The team has had 23 head coaches since organized football began in 1901 with the nickname Aggies. The team played without a head coach until 1905. The university, then known as Oklahoma Agricultural and Mechanical College, was renamed Oklahoma State University in 1957 and its nickname was changed to Cowboys. The Cowboys have played in more than 1,000 games during their 122 seasons. In those seasons, eight coaches have led the Cowboys to postseason bowl games: Jim Lookabaugh, Cliff Speegle, Jim Stanley, Jimmy Johnson, Pat Jones, Bob Simmons, Les Miles and Mike Gundy. Six coaches have won conference championships with the Cowboys: John Maulbetsch, Lynn Waldorf, Lookabaugh,, Stanley, and Gundy. Lookabaugh also won a national championship with the Cowboys.
Gundy is the all-time leader in games coached (245), wins (166) and years coached (19), while Waldorf is the all-time leader in winning percentage (.735). Theodore Cox finished his career with a .250 winning percentage, the worst in team history. Of the 23 Cowboy coaches, Maulbetsch, Waldorf, Exendine, and Johnson have been inducted in the College Football Hall of Fame. Three coaches are also graduates of the university: Lookabaugh, Floyd Gass, and Gundy. The first coach was F. A. McCoy, who coached only one season, in 1905. The current coach, Mike Gundy, was hired in January 2005.
| Number of coaches | |||
| CCs | Conference championships | ||
| NCs | National championships | ||
| bgcolor=#FFE6BD align="center" | † | Elected to the College Football Hall of Fame |
| GC | Games coached | |
| OW | Wins | |
| OL | Losses | |
| OT | Ties | |
| O% | Winning percentage |
| CW | Wins |
| CL | Losses |
| CT | Ties |
| C% | Winning percentage |
| PW | Wins |
| PL | Losses |
| PT | Ties |
Statistics correct as of the end of the 2023 NCAA Division I FBS football season
| 1 | 1905 | 7 | 1 | 4 | — | — | — | — | — | — | — | — | — | ||||||
| 2 | 1906–1907 | 15 | 2 | 9 | — | — | — | — | — | — | — | — | — | ||||||
| 3 | 1908 | 8 | 4 | 4 | — | — | — | — | — | — | — | — | — | — | |||||
| 4 | 1909–1914 | 45 | 28 | 16 | — | — | — | — | — | — | — | — | — | — | |||||
| 5 | 1915–1916 | 18 | 8 | 9 | .472 | — | — | — | — | — | — | ||||||||
| 6 | 1917–1918 | 15 | 8 | 7 | .533 | — | — | — | — | — | — | ||||||||
| 7 | 1919–1920 | 16 | 3 | 10 | .281 | — | — | — | — | — | — | ||||||||
| 8 | † | 1921–1928 | 70 | 27 | 37 | .429 | — | — | — | — | — | ||||||||
| 9 | † | 1929–1933 | 51 | 34 | 10 | .735 | — | — | — | — | — | ||||||||
| 10 | † | 1934–1935 | 20 | 7 | 12 | .375 | — | — | — | — | — | — | |||||||
| 11 | 1936–1938 | 30 | 7 | 23 | .233 | — | — | — | — | — | — | ||||||||
| 12 | 1939–1949 | 105 | 58 | 41 | .581 | 1–1945 | — | ||||||||||||
| 13 | 1950–1954 | 51 | 22 | 27 | .451 | — | — | — | — | — | |||||||||
| 14 | 1955–1962 | 81 | 36 | 42 | .463 | — | — | — | |||||||||||
| 15 | 1963–1968 | 59 | 19 | 38 | .339 | — | — | — | — | — | — | ||||||||
| 16 | 1969–1971 | 32 | 13 | 18 | .422 | — | — | — | — | — | 1969 Big 8 Coach of the Year[1] | ||||||||
| 17 | 1972 | 11 | 7 | 4 | .636 | — | — | — | — | — | — | ||||||||
| 18 | 1973–1978 | 68 | 35 | 31 | .529 | — | — | ||||||||||||
| 19 | † | 1979–1983 | 57 | 29 | 25 | .535 | — | — | |||||||||||
| 20 | 1984–1994 | 125 | 62 | 60 | .508 | — | — | — | |||||||||||
| 21 | 1995–2000 | 68 | 30 | 38 | .441 | — | — | ||||||||||||
| 22 | 2001–2004 | 49 | 28 | 21 | — | .571 | — | — | — | — | — | ||||||||
| 23 | 2005–present | — | — | — | — |