The Shady Side Academy boys soccer program is among the oldest in Western Pennsylvania, having started in 1928 with a four-game schedule. Two years later, play began in the Interstate Prep School League (IPSL). Shady Side joined the Western Pennsylvania Interscholastic Athletic League (WPIAL) in 1993, playing in both leagues until 1999. SSA has won a total of 20 IPSL titles and 11 WPIAL section titles. In 2010, the team opted to move up to WPIAL Class AA soccer after six years at the Class A level.