The 2009 US Squash National Coach of the Year, Jack Wyant came to Penn prior to the 2004-05 season as the head women's squash coach. Wyant was named Penn's Director of Squash before the 2018-19 season. Prior to this new role, Wyant spent six seasons as head coach of both the men's and women's teams.

In 2021-22, Wyant led Penn to a 19th straight Howe Cup appearance and a record of .500 or better for the 16th straight season. The Quakers picked up top-15 victories over Stanford, Williams, Bates, and Dartmouth and fell one match shy of a victory over Drexel, the eventual national runners-up.

2019-20 brought more success for Wyant and the Quakers, as he coached the team to yet another Howe Cup appearance. Under his leadership, Jessica Davis became just the 15th Quakers player to be named first-team All-America and marked the program's 14th straight season with a first-team All-American. Davis also took home first-team All-Ivy honors and was one of three CSA Scholar-Athletes.

After his final win of the 2017-18 season, Wyant became the women's program all-time wins leader as the Quakers defeated Columbia in the Howe Cup in his 152nd win with the program.

In 2015 and 2016, Wyant has led the women's squad to back-to-back second-place finishes in both the Ivy League and the Howe Cup. The Quakers were a combined 27-4 over the last two campaigns, reaching the Howe Cup championship match in consecutive seasons.

Individually, Wyant coached Reeham Salah to a national championship in 2018 - the program's first since 1996. Salah also won the CSA's Betty Richey Award which is the highest award given in women's squash.

One of the greatest players in program history, Gilly Lane C’07 was named the Head Coach of the men's squash program in March of 2016. Under his watch, Penn has put together a 66-23 record (26-9, Ivy League).

The Quakers made history in 2021-22 after not competing during the 2020-21 season, completing an undefeated regular season in which they were the wire-to-wire No. 1 team in the country, capped by the program’s first Ivy League title since the 1973-74 season and first undisputed league title since the 1968-69 season.

Penn’s 2021-22 highlights included Ivy League Coach of the Year honors for Lane, Ivy Rookie of the Year honors for Nathan Kueh, and first-team All-Ivy selections for Andrew Douglas and Aly Abou Eleinen, who were also named first-team All-Americans by the College Squash Association (CSA). Additionally, Penn beat Harvard for the first time since February of 2016, knocked off Trinity on the road for the first time since January of 1990, and won 10 matches by shutout, breaking the old record of nine set by the 2019-20 team.

In 2019-20, the Red and Blue reached the Potter Cup final for the first time in program history, defeating #2 Trinity in the semifinal for the first time since 1996. The Quakers also set several program records with nine shutout victories, Andrew Douglas being named the first three-time first-team All-American in program history and four total players named All-America.

The 2018-19 season proved to be one of the most successful in program history, Under Lane's watch, the program earned the No. 1 ranking in the CSA for the first time in program history and finished second in the Ivy League in 2018-19, earning their highest finish since 1986-87. The Quakers defeated Princeton and Yale in the same season and started 4-0 in Ivy League play for the first since 1973-74. Lane also led the Quakers to a win at Yale for the first time since his senior season. Penn went on to win 14 matches - the most in program history in a single season - and would go on to place third in the Potter Cup, its best finish in the national tournament in program history. Individually, Aly Abou Eleinen became just the third freshman in program history to be named first-team All-Ivy and First Team All-America. For a second straight season, Andrew Douglas earned first-team All-Ivy and All-America honors as well as he advanced to the semifinals at CSA Individuals.

Stuart Crawford was hired in January 2020 and just completed his first year as an assistant coach with the men’s and women’s squash programs at Penn.

Crawford came to Philadelphia after serving as an assistant coach at Amherst College for three seasons. Under his guidance, the Mammoths extended their run of consecutive Summers Cup appearances to ten seasons in a row, and in 2018-19 the program finished the season ranked #22 in the country.

Prior to his position at Amherst, Crawford coached overseas in his native Scotland. For the start of the 2015-16 season, Crawford was named Scottish National Coach. During that time, Crawford worked with several professional players while at the helm of Scottish Squash, including three top-40 players.

Following his retirement from professional squash in 2010, Crawford began his coaching career by joining Scottish Squash and serving as Assistant National Coach. Under his leadership, Crawford mentored the national junior program for five successful seasons before his promotion to National Coach.

A long-time professional squash player, Crawford was a five-time Scottish National Champion and a member of the Scottish National Team for 12 years. Crawford spent six years on the PSA Tour competing in events all over the globe. During his career, Crawford achieved a personal high World Ranking of 113 in February 2008. Crawford also recorded a PSA World Tour title by winning the Palasprint Open in Parma, Italy (November 2008).