[HCS]

I'm not 100 percent sure on the exact dates. This is from memory.
Cumberland, under Roger Morris, won regional titles from 1985 to 1991 and then in 93, so seven of eight years I think. The Harlan County teams were in the 14th Region in the 70s and part of the 80s. Cawood won the 14th Region in 82 and ended up losing to Middlesboro in the sectional finals.
Middlesboro won several titles in the late 90s - beat Cawood in the finals a couple of times. Rockcastle County also won one or two in the 90s or early 2000s. Harlan won in 96 and lost to Clay in the 97 finals.