| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||
| 1998 | 11/13 | 2A | Madison County | 47 | Eddie Dean | Lunenburg Central | 14 | Chippe Chappell | Madison | Eddie Dean Field | ||||
| 1998 | 11/13 | 2A | New Kent | 30 | Fred Birchett | King William | 6 | Roger Brookes | New Kent | |||||
| 1998 | 11/13 | 2A | Giles | 28 | Steve Ragsdale | Grayson County | 21 | Bill Strong | Pearisburg | Stephen C. Ragsdale Field | ||||
| 1998 | 11/13 | 2A | John Battle | 31 | Jimmy King | Floyd County | 12 | Winfred Beale | Bristol | |||||
| 1998 | 11/13 | 2A | Powhatan | 28 | Jim Woodson | Buffalo Gap | 20 | Bill Shirley | Powhatan | |||||
| 1998 | 11/14 | 2A | Powell Valley | 38 | Phil Robbins | Honaker | 19 | Doug Hubbard | Big Stone Gap | Bullitt Park | ||||
| 1998 | 11/14 | 2A | Clintwood | 35 | Bobby Meade | Haysi | 20 | James Colley | Haysi | |||||
| 1998 | 11/14 | 2A | Essex | 48 | Todd Jones | Arcadia | 17 | Bill Prince | Tappahannock | |||||
| 1998 | 11/20 | 2A | Giles | 36 | Steve Ragsdale | John Battle | 14 | Jimmy King | Bristol | |||||
| 1998 | 11/20 | 2A | Madison County | 21 | Eddie Dean | Powhatan | 15 | Jim Woodson | Madison | Eddie Dean Field | ||||
| 1998 | 11/21 | 2A | Powell Valley | 27 | Phil Robbins | Clintwood | 14 | Bobby Meade | Big Stone Gap | Bullitt Park | ||||
| 1998 | 11/21 | 2A | New Kent | 22 | Fred Birchett | Essex | 0 | Todd Jones | New Kent | |||||
| 1998 | 11/28 | 2A | Powell Valley | 40 | Phil Robbins | Giles | 0 | Steve Ragsdale | Pearisburg | Stephen C. Ragsdale Field | ||||
| 1998 | 11/28 | 2A | Madison County | 44 | Eddie Dean | New Kent | 22 | Fred Birchett | Madison | Eddie Dean Field | ||||
| 1998 | 12/5 | 2A | Powell Valley | 27 | Phil Robbins | Madison County | 14 | Eddie Dean | Harrisonburg | Bridgeforth Stadium | ||||
| 502 | 208 | |||||||||||||
| 33.47 | 13.87 | |||||||||||||