| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||
| 1998 | 11/13 | 3A | Tunstall | 21 | Buddy Brown | Gretna | 12 | Robert Prunty | Dry Fork | |||||
| 1998 | 11/13 | 3A | Rustburg | 37 | Mike Scharnus | Lord Botetourt | 20 | Tony Hart | Rustburg | |||||
| 1998 | 11/13 | 3A | Lebanon | 34 | John Adams | Laurel Park | 14 | Brad Lopez | Lebanon | Harry Stuart Field | ||||
| 1998 | 11/13 | 3A | Nottoway | 58 | Joe May | James Monroe | 7 | Rich Serbay | Nottoway | Nottoway Sports Complex | ||||
| 1998 | 11/13 | 3A | Graham | 28 | Glynn Carlock | Bassett | 7 | Ken Moran | Bassett | Ed Bassett Stadium | ||||
| 1998 | 11/14 | 3A | Matoaca | 21 | Pat Manuel | Bruton | 18 | Kyle Neve | Williamsburg | |||||
| 1998 | 11/14 | 3A | Waynesboro | 17 | C. J. DeWitt | Broadway | 7 | Rod Bowers | Broadway | |||||
| 1998 | 11/14 | 3A | Handley | 28 | Todd Hill | Fort Defiance | 16 | Dale Spitzer | Winchester | Handley Bowl | ||||
| 1998 | 11/20 | 3A | Rustburg | 14 | Mike Scharnus | Tunstall | 9 | Buddy Brown | Dry Fork | |||||
| 1998 | 11/21 | 3A | Graham | 41 | Glynn Carlock | Lebanon | 20 | John Adams | Lebanon | Harry Stuart Field | ||||
| 1998 | 11/21 | 3A | Handley | 20 | Todd Hill | Waynesboro | 13 | C. J. DeWitt | Winchester | Handley Bowl | ||||
| 1998 | 11/21 | 3A | Nottoway | 26 | Joe May | Matoaca | 20 | Pat Manuel | Nottoway | Nottoway Sports Complex | ||||
| 1998 | 11/28 | 3A | Rustburg | 42 | Mike Scharnus | Graham | 7 | Glynn Carlock | Rustburg | |||||
| 1998 | 11/28 | 3A | Nottoway | 18 | Joe May | Handley | 13 | Todd Hill | Nottoway | Nottoway Sports Complex | ||||
| 1998 | 12/5 | 3A | Nottoway | 44 | Joe May | Rustburg | 27 | Mike Scharnus | Charlottesville | Theodose Field | ||||
| 449 | 210 | |||||||||||||
| 29.93 | 14.00 | |||||||||||||