| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||
| 2000 | 11/10 | 5A | Culpeper County | 35 | Lou Sorrentino | Albemarle | 0 | Rick Vrhovac | Culpeper | |||||
| 2000 | 11/10 | 5A | West Potomac | 21 | John Howerton | Thomas Edison | 13 | Vaughn Lewis | Alexandria | |||||
| 2000 | 11/10 | 5A | Pulaski County | 30 | Joel Hicks | Patrick Henry Roanoke | 13 | Jeff Johnson | Dublin | Kenneth J. Dobson Stadium | ||||
| 2000 | 11/10 | 5A | Langley | 27 | John Iannucci | Mount Vernon | 0 | Jody Stone | McLean | |||||
| 2000 | 11/10 | 5A | Heritage Newport News | 26 | John Quillen | I. C. Norcom | 14 | Joe Langston | Newport News | Todd Stadium | ||||
| 2000 | 11/10 | 5A | Hopewell | 35 | Marshall Parker | Huguenot | 6 | Richard McFee | Hopewell | Merner Field | ||||
| 2000 | 11/10 | 5A | Hampton | 28 | Mike Smith | Lake Taylor | 12 | Hank Sawyer | Norfolk | Chittum Field | ||||
| 2000 | 11/10 | 5A | Dinwiddie | 25 | John Curia | Monacan | 7 | Keith Daniels | Dinwiddie | |||||
| 2000 | 11/17 | 5A | Heritage Newport News | 41 | John Quillen | Hampton | 0 | Mike Smith | Newport News | Todd Stadium | ||||
| 2000 | 11/17 | 5A | Dinwiddie | 28 | John Curia | Hopewell | 7 | Marshall Parker | Dinwiddie | |||||
| 2000 | 11/17 | 5A | Pulaski County | 28 | Joel Hicks | Culpeper County | 20 | Lou Sorrentino | Culpeper | Broman Field | ||||
| 2000 | 11/17 | 5A | West Potomac | 14 | John Howerton | Langley | 7 | John Iannucci | McLean | |||||
| 2000 | 11/25 | 5A | Dinwiddie | 28 | John Curia | West Potomac | 7 | John Howerton | Dinwiddie | |||||
| 2000 | 11/25 | 5A | Heritage Newport News | 22 | John Quillen | Pulaski County | 17 | Joel Hicks | Dublin | Kenneth J. Dobson Stadium | ||||
| 2000 | 12/2 | 5A | Heritage Newport News | 45 | John Quillen | Dinwiddie | 7 | John Curia | Richmond | University of Richmond Stadium | ||||
| 433 | 130 | |||||||||||||
| 28.87 | 8.67 | |||||||||||||