The Old Woodruff High School, located at 231 East Hayne Street in Woodruff, South Carolina, is a notable example of early 20th-century educational architecture. Designed by architects Frank H. Cunningham and Joseph G. Cunningham, the building was constructed in 1925 in the Collegiate Gothic style. Its distinctive features include a two-story, stuccoed masonry structure with a modified “H” plan, Gothic arches, and recessed entrances framed by pointed arches. ​

Initially serving as the town’s high school until 1953, the building subsequently functioned as a junior high and later an elementary school. In 1978, the City of Woodruff repurposed the structure to house its City Hall and Police Headquarters, preserving its historical significance while adapting it for modern civic use. ​

Recognizing its architectural and historical importance, the Old Woodruff High School was added to the National Register of Historic Places on October 18, 2006.