Varsity Squash competes against teams in the MIAA Conference. The team's home court is Coppermine Racket & Fitness Club. Coach Joe Lacy, entering his 10th season, and the pro from Coppermine hold practices every day in season and the teams usually have two matches a week, including a series of weekly challenge matches within the team.

The varsity squash team finished 3rd in the MIAA conference during the 2021–22 season. It was the best season in program history as the team earned wins against McDonogh, Boys’ Latin, Park, Friends, and Calvert Hall. The top player in the program, co-captain Matt Sullivan '22, was also recruited and accepted to play at Haverford College.

The varsity squash season begins each year with a scrimmage against the Naval Academy club squash team (the team earned a 4-3 victory in 2021) and also includes non-conference matches against Lancaster County Day School and UVA at the Boars Head Racket Club in Charlottesville, VA. The season continues with a competitive MIAA schedule and ends at the High School Nationals, held at Drexel University.

Loyola also has a Squash Club in the Middle School that meets three times a week after school, 2:45 p.m. until 3:30 p.m., for practices and matches.