Damron was the head coach Boyd County High School in Ashland, Kentucky from 2002 to 2005. The Lions advanced to the second round of the playoffs three straight years, going a combined 24-22 in 3 seasons at Boyd Co. In 2007, he was chosen to head the brand new football program at Kentucky Christian Knights located in Grayson, Kentucky. He held that position for the 2007 and 2008 seasons.His coaching record at Kentucky Christian was 3 wins and 13 losses. As of the conclusion of the 2009 season, this ranks him #1 at Kentucky Christian in total wins and #1 at the school in winning percentage (.188).