| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||||
| 1999 | 11/12 | 1A | Surry County | 39 | Willie Gillus | Rappahannock | 0 | Jerry Parrish | Dendron | |||||||
| 1999 | 11/12 | 1A | Strasburg | 42 | Glenn Proctor | Riverheads | 35 | Robert Casto | Greenville | |||||||
| 1999 | 11/12 | 1A | Pound | 46 | Rocky Baker | St. Paul | 6 | Tom Fletcher | Pound | Dotson-Mullins Field | ||||||
| 1999 | 11/12 | 1A | Narrows | 7 | Don Lowe | Covington | 3 | Brad Morton | Covington | Casey Field | ||||||
| 1999 | 11/13 | 1A | Rural Retreat | 21 | Dean Rhea | Northwood | 14 | Billy Wyatt | Saltville | |||||||
| 1999 | 11/13 | 1A | Garden | 16 | Roger Rife | Rye Cove | 14 | Joe Carter | Rye Cove | Eagles Nest | ||||||
| 1999 | 11/13 | 1A | Stonewall Jackson Q | 21 | Dick Krol | Lunenburg Central | 14 | Chippe Chappell | Victoria | Charger Stadium | ||||||
| 1999 | 11/13 | 1A | Sussex Central | 42 | Dwight Reagan | West Point | 8 | Lacy Norman | Sussex | Semones Field | ||||||
| 1999 | 11/19 | 1A | Stonewall Jackson Q | 22 | Dick Krol | Strasburg | 21 | Glenn Proctor | Quicksburg | |||||||
| 1999 | 11/19 | 1A | Rural Retreat | 49 | Dean Rhea | Narrows | 7 | Don Lowe | Rural Retreat | Community Stadium | ||||||
| 1999 | 11/20 | 1A | Pound | 48 | Rocky Baker | Garden | 6 | Roger Rife | Pound | Dotson-Mullins Field | ||||||
| 1999 | 11/20 | 1A | Surry County | 12 | Willie Gillus | Sussex Central | 6 | Dwight Reagan | Dendron | |||||||
| 1999 | 11/27 | 1A | Pound | 17 | Rocky Baker | Rural Retreat | 14 | Dean Rhea | Rural Retreat | Community Stadium | ||||||
| 1999 | 11/27 | 1A | Surry County | 41 | Willie Gillus | Stonewall Jackson Q | 13 | Dick Krol | Quicksburg | |||||||
| 1999 | 12/4 | 1A | Surry County | 21 | Willie Gillus | Pound | 6 | Rocky Baker | Lynchburg | Williams Stadium | ||||||
| 444 | 167 | |||||||||||||||
| 29.60 | 11.13 | |||||||||||||||