The first Chester High School building was erected in 1902.[2]
The district offers a wide variety of clubs, activities and sports. Sports programs include; football, basketball, volleyball, cheerleading, baseball, tennis, track and club activities. This school has a long-standing tradition of Championship wins in basketball. The Clippers have won eight state championships: 1983, 1989, 1994, 2000, 2005, 2008, 2011 and 2012. Chester was state runner-up in 1954, 1955, 1957, 1959, 1966, 1967, 1972, 2003, 2007 and 2013. Since the 1981-82 season, Chester has qualified for the state tournament every year except for 1991-92.
Louis A. Bloom, Pennsylvania State Representative for Delaware County (1947-1952), Judge of the Pennsylvania Court of Common Pleas, Delaware County
Ellwood J. Turner, Pennsylvania State Representative for Delaware County (1925-1948), 119th Speaker of the Pennsylvania House of Representatives (1939-1941)