| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||
| 2000 | 11/10 | 1A | Lunenburg Central | 20 | Chippe Chappell | Strasburg | 14 | Glenn Proctor | Victoria | Charger Stadium | ||||
| 2000 | 11/10 | 1A | Rural Retreat | 41 | Dean Rhea | Northwood | 6 | Billy Wyatt | Rural Retreat | Community Stadium | ||||
| 2000 | 11/10 | 1A | Surry County | 21 | Kermit Buggs | King & Queen Central | 14 | Rip Worrell | Dendron | |||||
| 2000 | 11/10 | 1A | Riverheads | 28 | Robert Casto | Stonewall Jackson Q | 16 | Dick Krol | Greenville | |||||
| 2000 | 11/10 | 1A | Bath County | 53 | Chris Jones | Eastern Montgomery | 14 | Brett McPherson | Hot Springs | Carl F. Williams Field | ||||
| 2000 | 11/10 | 1A | Appalachia | 14 | Tom Turner | Pound | 7 | Rocky Baker | Pound | Dotson-Mullins Field | ||||
| 2000 | 11/11 | 1A | Rye Cove | 24 | Bill Houseright | St. Paul | 6 | B. I. Salyers | St. Paul | Bowman Field | ||||
| 2000 | 11/11 | 1A | Sussex Central | 44 | Dwight Reagan | Mathews | 38 | Matt Lawson | Sussex | Semones Field | ||||
| 2000 | 11/17 | 1A | Riverheads | 31 | Robert Casto | Lunenburg Central | 28 | Chippe Chappell | Greenville | |||||
| 2000 | 11/17 | 1A | Bath County | 53 | Chris Jones | Rural Retreat | 28 | Dean Rhea | Hot Springs | Carl F. Williams Field | ||||
| 2000 | 11/18 | 1A | Surry County | 19 | Kermit Buggs | Sussex Central | 0 | Dwight Reagan | Sussex | Semones Field | ||||
| 2000 | 11/18 | 1A | Rye Cove | 20 | Bill Houseright | Appalachia | 14 | Tom Turner | Appalachia | Riggs Stadium | ||||
| 2000 | 11/25 | 1A | Bath County | 42 | Chris Jones | Rye Cove | 18 | Bill Houseright | Gate City | Legion Field | ||||
| 2000 | 11/25 | 1A | Riverheads | 17 | Robert Casto | Surry County | 0 | Kermit Buggs | Dendron | |||||
| 2000 | 12/2 | 1A | Riverheads | 26 | Robert Casto | Bath County | 12 | Chris Jones | Lynchburg | Williams Stadium | ||||
| 453 | 215 | |||||||||||||
| 30.20 | 14.33 | |||||||||||||