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1953: city runner-up

Chamberlain averaged 31 points per game during his 1953 high-school season and led his team to a 71–62 win over the Northeast High School team of Hall of Fame guard Guy Rodgers. Chamberlain scored 34 points as Overbrook won the Philadelphia Public League title and gained a spot in the city championship game against West Catholic High School, the winner of the rival Catholic league. In that game, West Catholic quadruple-teamed Chamberlain throughout the game, and despite his 29 points, the Hilltoppers lost 54–42.