| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||
| 2014 | 11/14 | 2A | Wilson Memorial | 49 | Jeremiah Major | Prince Edward County | 0 | Fishersville | ||||||
| 2014 | 11/14 | 2A | Union | 30 | Travis Turner | Tazewell | 20 | Shane Allen | Big Stone Gap | Bullitt Park | ||||
| 2014 | 11/14 | 2A | Richlands | 42 | Greg Mance | Lebanon | 7 | Phillip Henley | Richlands | Ernie Hicks Stadium | ||||
| 2014 | 11/14 | 2A | King William | 37 | Dylan Dehart | Strasburg | 12 | Mark Roller | King William | |||||
| 2014 | 11/14 | 2A | Gate City | 70 | Bill Houseright | Graham | 0 | Mike Williams | Gate City | Legion Field | ||||
| 2014 | 11/14 | 2A | Giles | 63 | Jeff Williams | Martinsville | 0 | Orion Martin | Pearisburg | Stephen C. Ragsdale Field | ||||
| 2014 | 11/14 | 2A | East Rockingham | 33 | Donnie Coleman | Robert E. Lee Staunton | 29 | David Tibbs | Elkton | |||||
| 2014 | 11/14 | 2A | Clarke County | 44 | Chris Parker | Nandua | 0 | Chris Miles | Berryville | Wilbur M. Feltner Stadium | ||||
| 2014 | 11/14 | 2A | Goochland | 56 | Joe Fowler | Buffalo Gap | 14 | Andy Cline | Goochland | |||||
| 2014 | 11/14 | 2A | Marion | 40 | Joey Carroll | Chatham | 21 | Paul Grekos | Marion | Hurricane Stadium | ||||
| 2014 | 11/14 | 2A | Glenvar | 13 | Kevin Clifford | Central Wise | 6 | Luke Owens | Salem | Highlander Stadium | ||||
| 2014 | 11/14 | 2A | Riverheads | 49 | Robert Casto | Bruton | 0 | Reggie Jones | Greenville | |||||
| 2014 | 11/14 | 2A | Buckingham County | 50 | Craig Gill | Dan River | 21 | Ferrell Edmunds | Buckingham | |||||
| 2014 | 11/14 | 2A | Nottoway | 14 | Grayson Throckmorton | Amelia County | 12 | Adam Tiller | Nottoway | Nottoway Sports Complex | ||||
| 2014 | 11/15 | 2A | Lee | 20 | Terry Martin | Appomattox County | 14 | Doug Smith | Appomattox | Bragg Stadium | ||||
| 2014 | 11/15 | 2A | Brunswick | 38 | Harold Williams | Luray | 7 | Travis Osborne | Lawrenceville | |||||
| 2014 | 11/21 | 2A | King William | 28 | Dylan Dehart | Riverheads | 27 | Robert Casto | Greenville | |||||
| 2014 | 11/21 | 2A | Nottoway | 13 | Grayson Throckmorton | Clarke County | 2 | Chris Parker | Berryville | Wilbur M. Feltner Stadium | ||||
| 2014 | 11/21 | 2A | Richlands | 41 | Greg Mance | Marion | 15 | Joey Carroll | Marion | Hurricane Stadium | ||||
| 2014 | 11/21 | 2A | Wilson Memorial | 42 | Jeremiah Major | East Rockingham | 7 | Donnie Coleman | Fishersville | |||||
| 2014 | 11/21 | 2A | Brunswick | 39 | Harold Williams | Goochland | 21 | Joe Fowler | Goochland | |||||
| 2014 | 11/22 | 2A | Gate City | 48 | Bill Houseright | Buckingham County | 13 | Craig Gill | Gate City | Legion Field | ||||
| 2014 | 11/22 | 2A | Glenvar | 19 | Kevin Clifford | Union | 9 | Travis Turner | Salem | Highlander Stadium | ||||
| 2014 | 11/22 | 2A | Giles | 49 | Jeff Williams | Lee | 14 | Terry Martin | Pearisburg | Stephen C. Ragsdale Field | ||||
| 2014 | 11/28 | 2A | Nottoway | 6 | Grayson Throckmorton | King William | 0 | Dylan Dehart | Nottoway | Nottoway Sports Complex | ||||
| 2014 | 11/29 | 2A | Wilson Memorial | 25 | Jeremiah Major | Brunswick | 6 | Harold Williams | Fishersville | Steve Geimon Stadium | ||||
| 2014 | 11/29 | 2A | Glenvar | 35 | Kevin Clifford | Giles | 0 | Jeff Williams | Pearisburg | Stephen C. Ragsdale Field | ||||
| 2014 | 11/29 | 2A | Richlands | 35 | Greg Mance | Gate City | 28 | Bill Houseright | Gate City | Legion Field | ||||
| 2014 | 12/6 | 2A | Wilson Memorial | 13 | Jeremiah Major | Richlands | 7 | Greg Mance | 1OT | Fishersville | Steve Geimon Stadium | |||
| 2014 | 12/6 | 2A | Glenvar | 37 | Kevin Clifford | Nottoway | 14 | Grayson Throckmorton | Salem | Highlander Stadium | ||||
| 2014 | 12/13 | 2A | Glenvar | 20 | Kevin Clifford | Wilson Memorial | 14 | Jeremiah Major | 1OT | Salem | Salem Stadium | |||
| 1,098 | 340 | |||||||||||||
| 35.42 | 10.97 | |||||||||||||