| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||||
| 1989 | 11/17 | 5A | Heritage Lynchburg | 14 | John Walker | E. C. Glass | 0 | Bo Henson | Lynchburg | City Stadium | ||||||
| 1989 | 11/17 | 5A | Thomas Edison | 21 | Dennis Randolph | George Marshall | 17 | Mike Skinner | Falls Church | Jimmie Miller Stadium | ||||||
| 1989 | 11/17 | 5A | Thomas Dale | 14 | Vic Williams | Meadowbrook | 10 | Jamie Accashian | Chester | J. Wilson Crump Stadium | ||||||
| 1989 | 11/17 | 5A | Potomac | 33 | Bill Brown | Stonewall Jackson M | 22 | Jim Powell | Dumfries | |||||||
| 1989 | 11/17 | 5A | Woodrow Wilson | 35 | Darnell Moore | Lake Taylor | 0 | Bill Morrow | Chesapeake | Western Branch High School | ||||||
| 1989 | 11/17 | 5A | Warwick | 27 | Bill Lyons | Deep Creek | 0 | Jim Garrett | Newport News | Todd Stadium | ||||||
| 1989 | 11/17 | 5A | Henrico | 24 | John Trott | Huguenot | 18 | Richard McFee | Henrico | Chappell Stadium | ||||||
| 1989 | 11/17 | 5A | J. E. B. Stuart | 49 | Tom Arehart, Sr. | Robert E. Lee Springfield | 26 | Steve Sengatack | Falls Church | Jerry Fauls Stadium | ||||||
| 1989 | 11/24 | 5A | Woodrow Wilson | 21 | Darnell Moore | Warwick | 14 | Bill Lyons | Chesapeake | Western Branch High School | ||||||
| 1989 | 11/25 | 5A | Potomac | 52 | Bill Brown | Heritage Lynchburg | 14 | John Walker | Dumfries | |||||||
| 1989 | 11/25 | 5A | J. E. B. Stuart | 42 | Tom Arehart, Sr. | Thomas Edison | 26 | Dennis Randolph | Fairfax | Pat Cunningham Stadium | ||||||
| 1989 | 11/25 | 5A | Thomas Dale | 21 | Vic Williams | Henrico | 12 | John Trott | Richmond | University of Richmond Stadium | ||||||
| 1989 | 12/2 | 5A | Potomac | 20 | Bill Brown | Thomas Dale | 14 | Vic Williams | Dumfries | |||||||
| 1989 | 12/2 | 5A | Woodrow Wilson | 35 | Darnell Moore | J. E. B. Stuart | 30 | Tom Arehart, Sr. | Arlington | War Memorial Sadium | ||||||
| 1989 | 12/16 | 5A | Woodrow Wilson | 20 | Darnell Moore | Potomac | 0 | Bill Brown | Chesapeake | Western Branch High School | postponed 1 week | |||||
| 428 | 203 | |||||||||||||||
| 28.53 | 13.53 | |||||||||||||||