Cleveland High School is located on the site of the home of Jesse Bushyhead (1804-1844), a Cherokee religious and political leader.

[5] In the late 1950s, a group of Cleveland citizens began working for a city high school.

The first step was taken when a ninth grade was added to Arnold Junior High, now an elementary school.

On May 12, 1965, voters passed a referendum that allowed for the issuing of $2 million in bonds for construction of the new high school.

[7] Every year during homecoming week, a parade is held on Raider Drive to commemorate the anniversary of this historic walk.

Henley, Charles Carrick, Maxine Hughes, Doug Greene, Ken Willey, and Chuck Rockholt.

[9] In December 2013, the Raider Dome, which was used as the school's main gymnasium was closed due to faults in the structure.

The program was awarded the NFHS Network's Best Overall School Broadcast Program at the NFHS convention in 2015,[16] and the "Best Daily Newscast in the Nation" by the Student Television Network (STN) in 2016 and 2017, breaking an eight-year streak of Carlsbad High School in California.