Squash is one of Yale's oldest intercollegiate sports. Yale began competition in 1920, commencing a rich tradition of championship players and teams that has continued to the present. The Bulldogs have captured 15 ISA Team Championships and have won nearly 85 percent of their dual matches. The man responsible for Yale's original success was John Skillman, a three-time professional champion who took over the Eli program in 1934 as its first head coach. Skillman spent the next 41 years as the Yale mentor while compiling a 451-77 record. His teams won 16 national titles and had just one losing season.

Brothers Sam '60 and Ralph Howe '63 each won U.S. singles and doubles titles. More recently, Victor Wagner '83 was an All-American for four years and won the Intercollegiate Championship in 1982. In 1986, Hugh LaBossier '86 won the U.S. National Hard Ball Championship. An All-American for three years, he received the Mallory Award as Yale's top male athlete and appeared in Sports Illustrated. In 1989, Will Carlin '85, an All-American for three years, won the U.S. National Soft Ball Championship.

Cyrus Mehta '90 and John Musto '91 earned first-team NISRA All-America and All-Ivy honors on a regular basis during their careers in New Haven. Garrett Frank '92 was a two-time first-team All-American. Reade Frank '94 was first-team All-America, All-Ivy and All-Academic, while Roger Arjoon '95 also was first team All-America, All-Ivy and Academic All-Ivy selection in addition to being selected as a Rhodes Scholar. Doug Lam '98 earned All-Ivy and honorable mention All-America honors, while Devraj Roy '98 was an Academic All-America selection as well as a member of the 1998 NISRA All-Tournament team. In 1999-2000, Kris Weiner '00 was an honorable-mention All-America selection, and in 2000-01 Peter Grote '02 and Anshul Manchanda '04 both earned first-team All-Ivy and second-team All-America honors. In 2001-02, Manchanda was first team All-Ivy and second team All-America. In 2002-03, Julian Illingworth '07 was a first-team All-America and All-Ivy selection, and Manchanda earned second-team All-America recognition. They both repeated these distinctions in 2003-04 and Illingworht accomplished the feat for the third time in 2004-05. J

The Elis captured two consecutive (1988-89, 1989-90) National Intercollegiate Squash Racquets Association regular season titles and post season championships. The 1988-89 championship was their first title in 27 years.