| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||
| 2008 | 11/7 | 5A | Lake Taylor | 24 | Hank Sawyer | Warwick | 17 | Stan Sexton | Norfolk | |||||
| 2008 | 11/7 | 5A | Thomas Edison | 37 | Vaughn Lewis | Robert E. Lee Springfield | 7 | Rob Everett | Alexandria | |||||
| 2008 | 11/7 | 5A | Stone Bridge | 42 | Mickey Thompson | Thomas Jefferson STEM | 0 | Tim Puvogel | Ashburn | |||||
| 2008 | 11/7 | 5A | Mount Vernon | 17 | Thomas Glynn | Washington - Lee | 10 | Josh Shapiro | Alexandria | Melvin B. Landes Stadium | ||||
| 2008 | 11/7 | 5A | James Madison | 28 | Gordon Leib | Yorktown | 7 | Bruce Hanson | Vienna | |||||
| 2008 | 11/7 | 5A | Green Run | 49 | Shawn Wilson | Grassfield | 17 | Martin Asprey | Virginia Beach | |||||
| 2008 | 11/7 | 5A | Phoebus | 63 | Bill Dee | Churchland | 6 | Cedric Cadle | Hampton | Darling Memorial Stadium | ||||
| 2008 | 11/8 | 5A | Hampton | 35 | Mike Smith | Indian River | 0 | Cadillac Harris | Hampton | Darling Memorial Stadium | ||||
| 2008 | 11/14 | 5A | Thomas Edison | 47 | Vaughn Lewis | James Madison | 7 | Gordon Leib | Alexandria | |||||
| 2008 | 11/14 | 5A | Stone Bridge | 42 | Mickey Thompson | Mount Vernon | 0 | Thomas Glynn | Ashburn | |||||
| 2008 | 11/14 | 5A | G. W. Danville | 27 | Dan Newell | Brooke Point | 21 | Jeff Berry | Stafford | |||||
| 2008 | 11/14 | 5A | Lake Taylor | 34 | Hank Sawyer | Hampton | 7 | Mike Smith | Norfolk | |||||
| 2008 | 11/14 | 5A | Phoebus | 47 | Bill Dee | Green Run | 0 | Shawn Wilson | Hampton | Darling Memorial Stadium | ||||
| 2008 | 11/15 | 5A | Liberty Bealeton | 35 | Tom Buzzo | William Fleming | 6 | Rob Senseney | Roanoke | Merrill Gainer Field | ||||
| 2008 | 11/17 | 5A | Dinwiddie | 38 | Billy Mills | Douglas Freeman | 7 | Bob Brinkley | Dinwiddie | |||||
| 2008 | 11/17 | 5A | Hanover | 24 | Joshua Just | Monacan | 14 | Danny Parsons | Mechanicsville | |||||
| 2008 | 11/21 | 5A | Liberty Bealeton | 41 | Tom Buzzo | G. W. Danville | 14 | Dan Newell | Bealeton | Kip Hull Field | ||||
| 2008 | 11/21 | 5A | Phoebus | 14 | Bill Dee | Lake Taylor | 0 | Hank Sawyer | Norfolk | Harbor Park | ||||
| 2008 | 11/21 | 5A | Stone Bridge | 35 | Mickey Thompson | Thomas Edison | 6 | Vaughn Lewis | Alexandria | |||||
| 2008 | 11/22 | 5A | Dinwiddie | 34 | Billy Mills | Hanover | 17 | Joshua Just | Dinwiddie | |||||
| 2008 | 11/29 | 5A | Dinwiddie | 42 | Billy Mills | Liberty Bealeton | 21 | Tom Buzzo | Dinwiddie | |||||
| 2008 | 11/29 | 5A | Phoebus | 38 | Bill Dee | Stone Bridge | 8 | Mickey Thompson | Hampton | Darling Memorial Stadium | ||||
| 2008 | 12/6 | 5A | Phoebus | 37 | Bill Dee | Dinwiddie | 13 | Billy Mills | Blacksburg | Lane Stadium | ||||
| 830 | 205 | |||||||||||||
| 36.09 | 8.91 | |||||||||||||