The region was first settled in the middle of the 1850s. Harrell Cundiff was one of the original settlers. In the 1860s, the prospect of Indian incursions drove many settlers off their homesteads. After the Indians were driven out of Jack County in the middle of the 1870s, people started moving back to the Cundiff region. It was not until the early 1890s that a permanent community was founded. Walker Moore established a townsite in 1891 and christened it Cundiff after dividing a large area of land into several farms. There was a post office in the town from 1891 to 1918. It also featured four businesses, a blacksmith shop, and a cotton gin around the turn of the century. The town's population stayed at about fifty from 1940 and 1988. It went down to 45 from 1990 through 2000.[2]
