| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||
| 2008 | 11/14 | 2A | Lebanon | 35 | John Adams | J. J. Kelly | 32 | B. I. Salyers | Lebanon | Harry Stuart Field | ||||
| 2008 | 11/14 | 2A | Floyd County | 15 | Winfred Beale | George Wythe Wytheville | 14 | Donnie Pruitt | Floyd | |||||
| 2008 | 11/14 | 2A | Washington & Lee | 19 | Malcolm Lewis | King William | 14 | Zach Just | Montross | |||||
| 2008 | 11/14 | 2A | Gretna | 36 | Chris Thurman | Goochland | 0 | Joe Fowler | Gretna | Lester Bond Field | ||||
| 2008 | 11/14 | 2A | Essex | 56 | Todd Jones | Northampton | 20 | Joe Ortelli | Tappahannock | |||||
| 2008 | 11/14 | 2A | Gate City | 28 | Nick Colobro | Powell Valley | 13 | Phil Robbins | Gate City | Legion Field | ||||
| 2008 | 11/14 | 2A | Chilhowie | 35 | Larry Russell | Giles | 17 | Jeff Williams | Chilhowie | |||||
| 2008 | 11/14 | 2A | Clarke County | 27 | Chris Parker | Appomattox County | 19 | Ben Martin | Berryville | |||||
| 2008 | 11/21 | 2A | Floyd County | 42 | Winfred Beale | Chilhowie | 13 | Larry Russell | Floyd | |||||
| 2008 | 11/21 | 2A | Gretna | 51 | Chris Thurman | Clarke County | 27 | Chris Parker | Gretna | Lester Bond Field | ||||
| 2008 | 11/22 | 2A | Essex | 34 | Todd Jones | Washington & Lee | 14 | Malcolm Lewis | Tappahannock | |||||
| 2008 | 11/22 | 2A | Lebanon | 19 | John Adams | Gate City | 13 | Nick Colobro | Wise | Carl Smith Stadium | ||||
| 2008 | 11/29 | 2A | Floyd County | 14 | Winfred Beale | Lebanon | 13 | John Adams | Floyd | |||||
| 2008 | 11/29 | 2A | Gretna | 45 | Chris Thurman | Essex | 40 | Todd Jones | Gretna | Lester Bond Field | ||||
| 2008 | 12/6 | 2A | Gretna | 35 | Chris Thurman | Floyd County | 20 | Winfred Beale | Salem | Salem Stadium | ||||
| 491 | 269 | |||||||||||||
| 32.73 | 17.93 | |||||||||||||