Woodlawn High School was organized in 1920 by a three-member grade school board which served as the Board for both Woodlawn Grade School and Woodlawn High School until the High School moved into its new building in 1949. The High School began as a two-year school, with a third year added in the fall of 1922. This school functioned as a three-year high school until 1939 when a state law required them to adopt a four-year program.
The first year there was only one teacher, Mr. T.D. Slater (also the principal). A second teacher was added the next two years, Mr. Willie Watkins. This arrangement lasted for several years.