| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||
| 1988 | 11/11 | 2A | Page County | 14 | Buddy Comer | Stuarts Draft | 13 | Bill Schindler | Stuarts Draft | |||||
| 1988 | 11/11 | 2A | Sussex Central | 74 | Dwight Reagan | Washington & Lee | 0 | Lee Sterner | Sussex | Semones Field | ||||
| 1988 | 11/11 | 2A | Lexington | 29 | Dennis Vaught | Chilhowie | 8 | Bill Clear | Chilhowie | |||||
| 1988 | 11/11 | 2A | Grayson County | 7 | Bill Strong | Floyd County | 0 | Winfred Beale | Independence | Bill Strong Field | ||||
| 1988 | 11/11 | 2A | New Kent | 21 | Fred Birchett | Arcadia | 0 | Keven Hall | Oak Hall | |||||
| 1988 | 11/12 | 2A | Honaker | 23 | Doug Hubbard | Powell Valley | 17 | Phil Robbins | 2OT | Big Stone Gap | Bullitt Park | |||
| 1988 | 11/12 | 2A | Lunenburg Central | 14 | Chippe Chappell | Fluvanna County | 7 | Steve Sheridan | Victoria | Charger Stadium | ||||
| 1988 | 11/12 | 2A | Pennington | 33 | Don Williams | Coeburn | 18 | Carl Richards | Pennington Gap | Robert E. Beeler, Jr. Stadium | ||||
| 1988 | 11/18 | 2A | Lexington | 21 | Dennis Vaught | Grayson County | 3 | Bill Strong | Independence | Bill Strong Field | ||||
| 1988 | 11/19 | 2A | Pennington | 14 | Don Williams | Honaker | 0 | Doug Hubbard | Pennington Gap | Robert E. Beeler, Jr. Stadium | ||||
| 1988 | 11/19 | 2A | Lunenburg Central | 34 | Chippe Chappell | Page County | 0 | Buddy Comer | Victoria | Charger Stadium | ||||
| 1988 | 11/19 | 2A | Sussex Central | 38 | Dwight Reagan | New Kent | 0 | Fred Birchett | Sussex | Semones Field | ||||
| 1988 | 11/26 | 2A | Lexington | 19 | Dennis Vaught | Pennington | 14 | Don Williams | Lexington | |||||
| 1988 | 11/26 | 2A | Lunenburg Central | 40 | Chippe Chappell | Sussex Central | 34 | Dwight Reagan | Victoria | Charger Stadium | ||||
| 1988 | 12/3 | 2A | Lexington | 18 | Dennis Vaught | Lunenburg Central | 13 | Chippe Chappell | Victoria | Charger Stadium | ||||
| 399 | 127 | |||||||||||||
| 26.60 | 8.47 | |||||||||||||