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The Holy Cross Crusaders football program is a college football team that represents the College of the Holy Cross in Worcester, Massachusetts. The team has had 29 head coaches since organized football began in 1896. The Crusaders have played in more than 1,200 games during their 123 seasons.

Holy Cross has played in one postseason bowl game, the 1946 Orange Bowl, under coach Ox DaGrosa. Since joining the Patriot League in 1986, three Holy Cross coaches have won conference championships: Mark Duffner, Tom Gilmore (American football) and Bob Chesney. Holy Cross does not claim any national championships in football.

Eddie Anderson is the Crusaders' all-time leader in years coached, games coached and wins. Among coaches to have served more than one season, Mark Duffner boasts the best winning percentage, while Bill Whitton recorded the worst.

Of the 29 Crusader coaches, four have been inducted in the College Football Hall of Fame. Rick E. Carter and Mark Duffner have each received National Coach of the Year honors from at least one organization. The current coach is Bob Chesney, who was hired in December 2017.

Coaches

 * Statistics correct as of the end of the 2019–20 college football season