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