1890: New city of Middlesborough held its first elections. There were two tickets, one sponsored by the American Association and headed by John Brooks, and the other led by local resident David Colson, who was said to be the largest landholder in the Yellow Creek Valley.
1898: Middlesboro City Council passed an ordinance prohibiting women from going in and out of any building where there was a saloon.
1917: “The Birth of a Nation” was playing at the Manring. It was accompanied by a 25 piece orchestra.
1927: The Independent Order of Bnai Brith of Knoxville met in Middlesboro. Over 100 people were present and $3600 was raised for Jewish relief.
1940: Blue Bell – Globe Overall plant was being dismantled and the machinery moved to Greensboro, North Carolina.
1965: State Highway Commissioner Henry Ward announced approval of a project to construct U.S. Highway 25E from Pineville to the Tennessee line.