| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||||
| 1999 | 11/12 | 5A | South Lakes | 25 | Dennis Randolph | West Potomac | 22 | Dale Eaton | Reston | Bergan Stadium | ||||||
| 1999 | 11/12 | 5A | Hampton | 58 | Mike Smith | Western Branch | 3 | Lew Johnston | Hampton | Darling Memorial Stadium | ||||||
| 1999 | 11/12 | 5A | Heritage Newport News | 20 | John Quillen | Norview | 0 | Carlton Thomas | Norfolk | Lake Taylor High School | ||||||
| 1999 | 11/12 | 5A | Yorktown | 38 | Bruce Hanson | Langley | 32 | John Iannucci | Arlington | |||||||
| 1999 | 11/12 | 5A | Henrico | 56 | David Bedwell | Huguenot | 20 | Richard McFee | Henrico | Chappell Stadium | ||||||
| 1999 | 11/12 | 5A | William Fleming | 28 | George Miller | Cave Spring | 6 | Ben Foutz | Roanoke | Victory Stadium | ||||||
| 1999 | 11/12 | 5A | Culpeper County | 17 | Lou Sorrentino | E. C. Glass | 7 | Dennis Peters | Culpeper | Broman Field | ||||||
| 1999 | 11/12 | 5A | Hopewell | 17 | Marshall Parker | George Wythe Richmond | 8 | Rodney Berry | Hopewell | Merner Field | ||||||
| 1999 | 11/19 | 5A | Henrico | 22 | David Bedwell | Hopewell | 16 | Marshall Parker | Hopewell | Merner Field | ||||||
| 1999 | 11/19 | 5A | Culpeper County | 29 | Lou Sorrentino | William Fleming | 8 | George Miller | Culpeper | Broman Field | ||||||
| 1999 | 11/19 | 5A | Yorktown | 40 | Bruce Hanson | South Lakes | 12 | Dennis Randolph | Reston | Bergan Stadium | ||||||
| 1999 | 11/19 | 5A | Hampton | 44 | Mike Smith | Heritage Newport News | 0 | John Quillen | Hampton | Darling Memorial Stadium | ||||||
| 1999 | 11/27 | 5A | Culpeper County | 20 | Lou Sorrentino | Hampton | 17 | Mike Smith | 1OT | Hampton | Darling Memorial Stadium | |||||
| 1999 | 11/27 | 5A | Henrico | 42 | David Bedwell | Yorktown | 0 | Bruce Hanson | Fairfax | Pat Cunningham Stadium | ||||||
| 1999 | 12/4 | 5A | Culpeper County | 21 | Lou Sorrentino | Henrico | 12 | David Bedwell | Richmond | University of Richmond Stadium | ||||||
| 477 | 163 | |||||||||||||||
| 31.80 | 10.87 | |||||||||||||||