| 1998-1999 |
Chesterfield County Henrico County Russell County New Horizons Regional Educational Center |
L.C. Bird High School J. R. Tucker High School Russell County Technology Center New Horizons Regional Educational Center |
| 1999-2000 |
Loudoun County Prince William County Waynesboro City |
C. S. Monroe Technology Center Gar-Field High School Waynesboro High School |
| 2000-2001 |
Danville City Norfolk City Rockbridge County Tazewell County |
George Washington High School Norfolk Technical Center Rockbridge High School Tazewell County Career & Technical Center |
| 2001-2002 |
Buena Vista City Colonial Heights Richmond City Scott County |
Parry McCluer High School Colonial Heights High School Richmond Technical Center Scott County Technical Center |