In his book, Chickasha...A Journey Back in Time, Irvin Munn quotes Mrs. Joe Dews as reporting that school in Chickasha was held in a store on Main Street with Eugene Hamilton, a lawyer, as teacher.

In her book, Trails, Rails, and School Tales, author Gwen Jackson quotes two sources that Chickasha was "one of the leading school systems in Oklahoma.

"[5] Chickasha High School has primarily occupied two locations: 1000 South 9th Street where the current Middle School is located and, in 1968, the current site of Chickasha High School was established, 101 N. John P. Cowan Ave formerly known as Borden Park.

After several unsuccessful attempts to pass bond issues, in 2003, the Chickasha High School Activity Center was completed.

[6] As well as the traditional curriculum options, Chickasha High School has an associated alternative education program, Quality Academy, which was housed off campus at the former Southwest Elementary School.