The first regular school in Oologah began in 1892 as a 3-month term in a small building west of the present Methodist Church near the creek. Seventeen students attended. The next 3-month term was taught in a building east of the railroad tracks. In 1893, the first regular school building was erected with donations and located east of town. Three-month terms were taught each spring and fall from 1893-1895. In September of 1895 Donna Ross, a granddaughter of Cherokee Chief John Ross, taught the first 9 months school term. This was known as the Cherokee School and was financed from Indian funds. White children paid one dollar per month tuition.

In September 1898, J.C. White taught a subscription school named NorthEast High located on the east side of town. The Indian school was called "Rawhide College".