Olean High School was built in 1935 and opened on February 22, 1937.

Due to economics hardships affecting the State of New York since the onset of the Great Recession, the school district began to see steep cuts from the state, and in order to maintain all of its operations, its budgets were continually downsized since 2008.

Olean High School was traditionally grades 9-12 up until the finish of the 2011–2012 academic year.

Following the end of the 2012 academic year, Olean High School now operates as grades 8–12.

Olean High School offers golf, basketball, baseball, softball, football, volleyball, soccer, tennis, wrestling, cross country, swimming, cheerleading, and track and field.