1861: General Zollicoffer ordered his regiments, which were stationed at the Cumberland Gap, into Kentucky after learning the neutrality of Kentucky had been breached in the west by General U.S. Grant. They were met by John C. Colson, Sr. and his Yellow Creek Home Guards in a brief skirmish.
1863: Surrounded by Union troops, General Frazier was tricked into surrendering 2000 troops that were stationed at the Gap without a fight.
1888: Lot on the southwest corner of Cumberland Avenue and 21st Street was purchased by A. D. Campbell from the Middlesborough Town Company, the office of which was located in Knoxville.
1890: Middlesborough had 83 business houses already erected and another 72 under construction. Seven hotels were open and receiving guests.
1897: Thomas Jones, a leading black businessman, announced his candidacy for City Council. He was endorsed by the local newspaper.
1926: All the stores in Middlesboro closed for Rosh Hashanah, the Jewish New Year.
1937: The classified section of the newspaper advertised “steady work” for two women or girls at $1.50 weekly.
1986: Middlesboro City Hall and the Fire Department were totally destroyed by fire.