1999
Boyle County 24 Pikeville 0
Pike County Bowl
WYMT Broadcast
August 21, 1999
Pikeville 39 Prestonsburg 0
WPRG Broadcast
August 27, 1999
Pikeville 73 Elkhorn City 6
September 3, 1999
Pikeville 56 Hazard 20
September 10, 1999
Pikeville 47 South Floyd 22
WPRG Broadcast
September 17, 1999
Pikeville 26 Belfry 8
WPRG Broadcast
September 24, 1999
Pikeville 74 Jenkins 0
October 9, 1999
Pikeville 49 Paintsville 11
WPRG Broadcast
October 29, 1999
Pikeville 66 Pineville 14
Class A Playoffs - Region IV Quarterfinals
WPRG Broadcast
November 5, 1999
Pikeville 41 Paintsville 15
Class A Playoffs - Region IV Semifinals
WPRG Broadcast
November 12, 1999
Pikeville 33 Harlan 12
Class A Playoffs - Region IV Championship
WPRG Broadcast
November 19, 1999
Beechwood 25 Pikeville 19
Class A Playoffs - State Semifinals
November 26, 1999