| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||
| 2000 | 11/10 | 2A | New Kent | 28 | Fred Birchett | Washington & Lee | 0 | Malcolm Lewis | New Kent | |||||
| 2000 | 11/10 | 2A | Giles | 36 | Steve Ragsdale | Grayson County | 21 | Bill Strong | Pearisburg | Stephen C. Ragsdale Field | ||||
| 2000 | 11/10 | 2A | Powell Valley | 23 | Phil Robbins | J. J. Kelly | 13 | Kevin Saunders | Big Stone Gap | Bullitt Park | ||||
| 2000 | 11/10 | 2A | Radford | 3 | Norman Lineburg | George Wythe Wytheville | 0 | Donnie Pruitt | Wytheville | Pendleton Field | ||||
| 2000 | 11/10 | 2A | Madison County | 14 | Eddie Dean | Brentsville District | 6 | Mike Madison | Madison | Eddie Dean Field | ||||
| 2000 | 11/10 | 2A | Buffalo Gap | 39 | Max Lowe | Amelia County | 0 | Torecco Greenbow | Swoope | |||||
| 2000 | 11/11 | 2A | King William | 40 | Roger Brookes | Arcadia | 14 | Bill Prince | King William | |||||
| 2000 | 11/11 | 2A | Honaker | 39 | Doug Hubbard | Haysi | 0 | James Colley | Honaker | Fuller Field | ||||
| 2000 | 11/17 | 2A | Giles | 20 | Steve Ragsdale | Radford | 6 | Norman Lineburg | Pearisburg | Stephen C. Ragsdale Field | ||||
| 2000 | 11/17 | 2A | Buffalo Gap | 22 | Max Lowe | Madison County | 21 | Eddie Dean | Madison | Eddie Dean Field | ||||
| 2000 | 11/18 | 2A | Honaker | 28 | Doug Hubbard | Powell Valley | 6 | Phil Robbins | Honaker | Fuller Field | ||||
| 2000 | 11/18 | 2A | King William | 6 | Roger Brookes | New Kent | 0 | Fred Birchett | New Kent | |||||
| 2000 | 11/25 | 2A | Honaker | 21 | Doug Hubbard | Giles | 9 | Steve Ragsdale | Pearisburg | Stephen C. Ragsdale Field | ||||
| 2000 | 11/25 | 2A | King William | 44 | Roger Brookes | Buffalo Gap | 0 | Max Lowe | Swoope | |||||
| 2000 | 12/2 | 2A | King William | 25 | Roger Brookes | Honaker | 15 | Doug Hubbard | Lynchburg | Williams Stadium | ||||
| 388 | 111 | |||||||||||||
| 25.87 | 7.40 | |||||||||||||