| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||
| 1996 | 11/15 | 2A | Northumberland | 12 | Mac Magerko | Washington & Lee | 9 | Malcolm Lewis | Heathsville | |||||
| 1996 | 11/15 | 2A | Randolph Henry | 26 | Jay Graves | Lunenburg Central | 12 | Chippe Chappell | Charlotte Court House | |||||
| 1996 | 11/15 | 2A | King William | 26 | Roger Brookes | Essex | 21 | Todd Jones | King William | |||||
| 1996 | 11/15 | 2A | Giles | 35 | Steve Ragsdale | Patrick Henry Glade | 13 | Ritchie Thomas | Pearisburg | Stephen C. Ragsdale Field | ||||
| 1996 | 11/16 | 2A | Chilhowie | 34 | Mike Sturgill | Grayson County | 7 | Bill Strong | Chilhowie | |||||
| 1996 | 11/15 | 2A | Powell Valley | 14 | Phil Robbins | Clintwood | 7 | Bobby Meade | Clintwood | Ralph Cummins Stadium | ||||
| 1996 | 11/16 | 2A | Powhatan | 51 | Jim Woodson | Madison County | 22 | Eddie Dean | Madison | Eddie Dean Field | ||||
| 1996 | 11/16 | 2A | Hurley | 18 | Wayne Hall | Haysi | 6 | James Colley | Haysi | |||||
| 1996 | 11/22 | 2A | Giles | 30 | Steve Ragsdale | Chilhowie | 15 | Mike Sturgill | Pearisburg | Stephen C. Ragsdale Field | ||||
| 1996 | 11/22 | 2A | Powhatan | 10 | Jim Woodson | Randolph Henry | 7 | Jay Graves | Charlotte Court House | |||||
| 1996 | 11/23 | 2A | Northumberland | 47 | Mac Magerko | King William | 26 | Roger Brookes | Heathsville | |||||
| 1996 | 11/23 | 2A | Powell Valley | 67 | Phil Robbins | Hurley | 18 | Wayne Hall | Big Stone Gap | Bullitt Park | ||||
| 1996 | 11/30 | 2A | Giles | 14 | Steve Ragsdale | Powell Valley | 7 | Phil Robbins | Pearisburg | Stephen C. Ragsdale Field | ||||
| 1996 | 11/30 | 2A | Powhatan | 22 | Jim Woodson | Northumberland | 14 | Mac Magerko | Powhatan | |||||
| 1996 | 12/7 | 2A | Powhatan | 20 | Jim Woodson | Giles | 8 | Steve Ragsdale | Midlothian | Midlothian High School | ||||
| 426 | 192 | |||||||||||||
| 28.40 | 12.80 | |||||||||||||