| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||||
| 1999 | 11/12 | 2A | Floyd County | 34 | Winfred Beale | Patrick Henry Glade | 7 | Ritchie Thomas | Floyd | |||||||
| 1999 | 11/12 | 2A | Essex | 1 | Todd Jones | New Kent | 0 | Fred Birchett | New Kent | Forfeit - original score 7-6 | ||||||
| 1999 | 11/12 | 2A | Clintwood | 18 | Bobby Meade | Powell Valley | 13 | Phil Robbins | Big Stone Gap | Bullitt Park | ||||||
| 1999 | 11/12 | 2A | George Wythe Wytheville | 40 | Larry Russell | Grayson County | 14 | Bill Strong | Wytheville | Pendleton Field | ||||||
| 1999 | 11/12 | 2A | Brentsville District | 39 | Mike Madison | Buckingham County | 21 | Craig Gill | Nokesville | |||||||
| 1999 | 11/12 | 2A | Madison County | 48 | Eddie Dean | Buffalo Gap | 7 | Max Lowe | Madison | Eddie Dean Field | ||||||
| 1999 | 11/13 | 2A | Honaker | 59 | Doug Hubbard | Haysi | 8 | James Colley | Honaker | Fuller Field | ||||||
| 1999 | 11/13 | 2A | King William | 82 | Roger Brookes | Arcadia | 0 | Bill Prince | King William | |||||||
| 1999 | 11/19 | 2A | Floyd County | 28 | Winfred Beale | George Wythe Wytheville | 6 | Larry Russell | Floyd | |||||||
| 1999 | 11/19 | 2A | Madison County | 27 | Eddie Dean | Brentsville District | 12 | Mike Madison | Madison | |||||||
| 1999 | 11/20 | 2A | Honaker | 20 | Doug Hubbard | Clintwood | 19 | Bobby Meade | 1OT | Honaker | Fuller Field | |||||
| 1999 | 11/20 | 2A | King William | 1 | Roger Brookes | New Kent | 0 | Fred Birchett | New Kent | forfeit - original score 6-30 | ||||||
| 1999 | 11/27 | 2A | Madison County | 34 | Eddie Dean | New Kent | 33 | Fred Birchett | New Kent | |||||||
| 1999 | 11/27 | 2A | Floyd County | 35 | Winfred Beale | Honaker | 32 | Doug Hubbard | Honaker | Fuller Field | ||||||
| 1999 | 12/4 | 2A | Madison County | 29 | Eddie Dean | Floyd County | 12 | Winfred Beale | Lynchburg | Williams Stadium | ||||||
| 495 | 184 | |||||||||||||||
| 33.00 | 12.27 | |||||||||||||||