| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||||
| 1991 | 11/15 | 5A | Albemarle | 7 | John Howdy Mack | Cave Spring | 0 | Jerry Little | Roanoke | Dwight Bogle Stadium | ||||||
| 1991 | 11/15 | 5A | Woodrow Wilson | 20 | Darnell Moore | Indian River | 14 | Lee Fowler | Chesapeake | Western Branch High School | ||||||
| 1991 | 11/15 | 5A | West Potomac | 33 | Dan Meier | Centreville | 21 | Neil Callahan | Alexandria | |||||||
| 1991 | 11/15 | 5A | Langley | 14 | Fred Benevento | Yorktown | 13 | Bruce Hanson | McLean | |||||||
| 1991 | 11/15 | 5A | John Marshall | 17 | Murray Wood | Dinwiddie | 14 | Cary Parker | Richmond | Hovey Field | ||||||
| 1991 | 11/15 | 5A | Patrick Henry Ashland | 28 | Ray Long, Jr. | Henrico | 23 | Dave Cooper | Ashland | Durham-Feal Athletic Field | ||||||
| 1991 | 11/15 | 5A | E. C. Glass | 38 | Bo Henson | Stonewall Jackson M | 0 | Jim Powell | Lynchburg | City Stadium | ||||||
| 1991 | 11/15 | 5A | I. C. Norcom | 25 | Joe Langston | Bethel | 8 | Dennis Kozlowski | Hampton | Darling Memorial Stadium | ||||||
| 1991 | 11/22 | 5A | Langley | 17 | Fred Benevento | West Potomac | 7 | Dan Meier | Arlington | War Memorial Sadium | ||||||
| 1991 | 11/22 | 5A | Woodrow Wilson | 21 | Darnell Moore | I. C. Norcom | 0 | Joe Langston | Chesapeake | Western Branch High School | ||||||
| 1991 | 11/22 | 5A | E. C. Glass | 14 | Bo Henson | Albemarle | 0 | John Howdy Mack | Lynchburg | City Stadium | ||||||
| 1991 | 11/23 | 5A | John Marshall | 16 | Murray Wood | Patrick Henry Ashland | 15 | Ray Long, Jr. | Richmond | University of Richmond Stadium | ||||||
| 1991 | 11/30 | 5A | E. C. Glass | 12 | Bo Henson | Langley | 6 | Fred Benevento | Arlington | |||||||
| 1991 | 11/30 | 5A | Woodrow Wilson | 34 | Darnell Moore | John Marshall | 0 | Murray Wood | Chesapeake | Western Branch High School | ||||||
| 1991 | 12/7 | 5A | Woodrow Wilson | 43 | Darnell Moore | E. C. Glass | 0 | Bo Henson | Chesapeake | Western Branch High School | ||||||
| 339 | 121 | |||||||||||||||
| 22.60 | 8.07 | |||||||||||||||