[2] A new, three-story brick building, designed to be the "largest and handsomest" school in Mississippi, was completed at the same location in 1921.

CHS was the sponsor of Cleveland's first Boy Scout troop, and, at various times, served as the meeting place of the First Methodist Church, the local Jewish community, the Rotary Club, the Exchange Club, and the Delta Medical Association.

[2] Integrated in 1965, CHS was the first public school in the Mississippi Delta to admit black students.

[3] In 2000, hundreds of alumni, students, and parents volunteered thousands of man-hours giving the school a much-needed makeover.

[2] In October 2008, a Mississippi Historical Marker honoring Margaret Wade ('29) was placed on the school's front lawn.

Principal Steven Craddock commented: "this proves what we have known for some time...that our students are just as sharp as teens in other, more affluent parts of our state...it also shows that CHS is striving to live up to our motto, 'Ever to Excel'.

Cleveland High maintains programs in soccer, cross country, track and field, football, basketball, swimming, baseball, softball, cheerleading, dance, volleyball, and powerlifting, as well as a competitive marching and concert band program.