| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||||
| 1999 | 11/12 | 6A | Varina | 28 | Gary Chilcoat | Lee-Davis | 0 | Mac McConnell | Richmond | Blue Devil Stadium | ||||||
| 1999 | 11/12 | 6A | Lake Braddock | 17 | Frances Dall | James Robinson | 0 | Mark Bendorf | Burke | Richard M. Lewis Memorial Stadium | ||||||
| 1999 | 11/12 | 6A | Patrick Henry Ashland | 44 | Ray Long, Jr. | L. C. Bird | 20 | Ron Paquette | Chesterfield | |||||||
| 1999 | 11/12 | 6A | North Stafford | 23 | Chris Beatty | G. W. Danville | 21 | Eddie Martin | Danville | J. T. Christopher Stadium | ||||||
| 1999 | 11/12 | 6A | Princess Anne | 23 | Jeff Ballance | Deep Creek | 7 | David Cox | Chesapeake | Tiger Stadium | ||||||
| 1999 | 11/12 | 6A | Centreville | 28 | Mike Skinner | Fairfax | 12 | Tom Verbanic | Fairfax | Harold Stalnaker Stadium | ||||||
| 1999 | 11/12 | 6A | C. D. Hylton | 20 | Bill Brown | Gar-Field | 0 | Tony Labozzetta | Woodbridge | |||||||
| 1999 | 11/12 | 6A | Bayside | 39 | Robert Jackson | Ocean Lakes | 9 | Jim Prince | Virginia Beach | Floyd Kellam High School | ||||||
| 1999 | 11/19 | 6A | Princess Anne | 19 | Jeff Ballance | Bayside | 0 | Robert Jackson | Virginia Beach | Floyd Kellam High School | ||||||
| 1999 | 11/19 | 6A | Varina | 41 | Gary Chilcoat | Patrick Henry Ashland | 21 | Ray Long, Jr. | Richmond | Blue Devil Stadium | ||||||
| 1999 | 11/20 | 6A | Centreville | 21 | Mike Skinner | Lake Braddock | 17 | Francis Dall | Fairfax | Pat Cunningham Stadium | ||||||
| 1999 | 11/20 | 6A | C. D. Hylton | 24 | Bill Brown | North Stafford | 6 | Chris Beatty | Woodbridge | |||||||
| 1999 | 11/27 | 6A | C. D. Hylton | 38 | Bill Brown | Princess Anne | 13 | Jeff Ballance | Woodbridge | |||||||
| 1999 | 11/27 | 6A | Varina | 23 | Gary Chilcoat | Centreville | 17 | Mike Skinner | Richmond | Blue Devil Stadium | ||||||
| 1999 | 12/4 | 6A | C. D. Hylton | 28 | Bill Brown | Varina | 27 | Gary Chilcoat | Richmond | University of Richmond Stadium | ||||||
| 416 | 170 | |||||||||||||||
| 27.73 | 11.33 | |||||||||||||||