The school was expanded with a new north wing in 1958, featuring a new metal shop classroom, and facilities for art, band and choir, paid for by a citywide bond issue approved in 1955.

[3][4][5] A new $1.25 million gymnasium and administrative offices were dedicated by Mayor Wes Uhlman and Lieutenant Governor John Cherberg in 1970.

[8] Students and faculty were strongly opposed to the closure plan, and it was ultimately modified to keep Cleveland open as a high school.

The project was completed in September 2007, after complications arising from asbestos found in ceilings and unexpected geological hazards below the school building.

[12] Cleveland High School is still housed in its original 1927 building, designed in the 20th century Neo-Georgian style by Floyd Naramore, who would later become a founding member of NBBJ.

[4] The high school, located atop southwestern Beacon Hill, overlooks Georgetown, the Duwamish River valley, Boeing Field, and Interstate 5.

In 2024, the school had 889 students, of which the racial demographics were 46% Asian, 21% Black, 12.5% White, 10.6% Hispanic, 9% Multiracial, 0.3% Pacific Islander, 0.2% Native American, and 0.3% from other races.

By 2009 Cleveland retained the Global Studies and HEAL academies, but overall academic improvement remained elusive, with a 56.7% graduation rate (on time or otherwise).