| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||
| 2000 | 11/10 | 3A | Rustburg | 28 | Mike Scharnus | William Campbell | 0 | Brad Bradley | Naruna | |||||
| 2000 | 11/10 | 3A | Gate City | 37 | Nick Colobro | Graham | 25 | Glynn Carlock | Gate City | Legion Field | ||||
| 2000 | 11/10 | 3A | Liberty Bedford | 40 | Scott Abell | Brookville | 19 | Bobby Johnson | Bedford | Minutemen Stadium | ||||
| 2000 | 11/10 | 3A | Grundy | 39 | Greg Rowe | Tazewell | 14 | Harris Hart | Grundy | Nelson Memorial Field | ||||
| 2000 | 11/10 | 3A | Turner Ashby | 46 | Joe Taylor | Fluvanna County | 21 | Tap Pace | Bridgewater | |||||
| 2000 | 11/10 | 3A | Handley | 19 | Todd Hill | Robert E. Lee Staunton | 16 | David Tibbs | Staunton | Staunton Memorial Stadium | ||||
| 2000 | 11/11 | 3A | Southampton | 42 | Littleton Parker | Bruton | 21 | Kyle Neve | Courtland | Arrowhead Stadium | ||||
| 2000 | 11/11 | 3A | Matoaca | 32 | Pat Manuel | Nottoway | 0 | Joe May | Nottoway | Nottoway Sports Complex | ||||
| 2000 | 11/17 | 3A | Gate City | 42 | Nick Colobro | Grundy | 12 | Greg Rowe | Gate City | Legion Field | ||||
| 2000 | 11/17 | 3A | Rustburg | 44 | Mike Scharnus | Liberty Bedford | 7 | Scott Abell | Bedford | Minutemen Stadium | ||||
| 2000 | 11/18 | 3A | Southampton | 10 | Littleton Parker | Matoaca | 8 | Pat Manuel | Courtland | |||||
| 2000 | 11/18 | 3A | Turner Ashby | 9 | Joe Taylor | Handley | 7 | Todd Hill | Bridgewater | |||||
| 2000 | 11/25 | 3A | Turner Ashby | 13 | Joe Taylor | Southampton | 0 | Littleton Parker | Courtland | |||||
| 2000 | 11/25 | 3A | Rustburg | 7 | Mike Scharnus | Gate City | 0 | Nick Colobro | Rustburg | |||||
| 2000 | 12/2 | 3A | Rustburg | 9 | Mike Scharnus | Turner Ashby | 6 | Joe Taylor | Harrisonburg | Bridgeforth Stadium | ||||
| 417 | 156 | |||||||||||||
| 27.80 | 10.40 | |||||||||||||