| Year | Date | Class | Winning Teams | Pts | Coach | Losing Teams | Pts | Coach | OT | Location | Field | Notes | ||
| 2019 | 11/15 | 2A | Ridgeview | 49 | Rick Mullins | Marion | 7 | Tim Smith | Clintwood | Ridgeview Stadium | ||||
| 2019 | 11/15 | 2A | Radford | 35 | Matthew Saunders | Patrick County | 0 | David Morrison | Radford | |||||
| 2019 | 11/15 | 2A | Union | 20 | Travis Turner | Gate City | 19 | Jeremy Houseright | Big Stone Gap | Bullitt Park | ||||
| 2019 | 11/15 | 2A | Strasburg | 38 | Mark Roller | Luray | 21 | Nolan Jeffries | Luray | Bulldog Field | ||||
| 2019 | 11/15 | 2A | Greensville County | 36 | Mario Walton | Nottoway | 28 | Glen Pettis | Emporia | |||||
| 2019 | 11/15 | 2A | Poquoson | 43 | Elliott Duty | John Marshall | 22 | Phillip Sims | Poquoson | |||||
| 2019 | 11/15 | 2A | Glenvar | 24 | Kevin Clifford | Floyd County | 0 | Winfred Beale | Salem | Highlander Stadium | ||||
| 2019 | 11/15 | 2A | East Rockingham | 41 | Donnie Coleman | Clarke County | 7 | Chris Parker | Berryville | Wilbur M. Feltner Stadium | ||||
| 2019 | 11/15 | 2A | Central Wise | 28 | Luke Owens | Richlands | 16 | Greg Mance | Wise | |||||
| 2019 | 11/15 | 2A | Gretna | 42 | Cole Simpson | Dan River | 0 | Brian Womack | Gretna | Lester Bond Field | ||||
| 2019 | 11/15 | 2A | Stuarts Draft | 23 | Nathan Floyd | Buffalo Gap | 6 | Brad Wygant | Stuarts Draft | |||||
| 2019 | 11/15 | 2A | Appomattox County | 64 | Doug Smith | Chatham | 22 | Matt Allen | Appomattox | Bragg Stadium | ||||
| 2019 | 11/15 | 2A | Buckingham County | 20 | Seth Wilkerson | Page County | 19 | Joey Soltis | 1OT | Buckingham | ||||
| 2019 | 11/15 | 2A | King William | 60 | Dylan Dehart | Amelia County | 12 | Mark Johnson | King William | Roger G. Brookes Field | ||||
| 2019 | 11/16 | 2A | Thomas Jefferson R | 49 | P. J. Adams | Brunswick | 12 | Harold Williams | Richmond | Huguenot High School | ||||
| 2019 | 11/16 | 2A | Graham | 42 | Tony Palmer | Tazewell | 14 | J'me Harris | Bluefield | Mitchell Stadium | ||||
| 2019 | 11/22 | 2A | Thomas Jefferson R | 44 | P. J. Adams | Greensville County | 18 | Mario Walton | Richmond | Huguenot High School | ||||
| 2019 | 11/22 | 2A | Stuarts Draft | 28 | Nathan Floyd | Strasburg | 14 | Mark Roller | Stuarts Draft | |||||
| 2019 | 11/22 | 2A | Central Wise | 14 | Luke Owens | Ridgeview | 7 | Rick Mullins | Clintwood | Ridgeview Stadium | ||||
| 2019 | 11/22 | 2A | East Rockingham | 41 | Donnie Coleman | Buckingham County | 17 | Seth Wilkerson | Buckingham | |||||
| 2019 | 11/22 | 2A | King William | 46 | Dylan Dehart | Poquoson | 20 | Elliott Duty | King William | Roger G. Brookes Field | ||||
| 2019 | 11/22 | 2A | Graham | 48 | Tony Palmer | Union | 7 | Travis Turner | Big Stone Gap | Bullitt Park | ||||
| 2019 | 11/22 | 2A | Gretna | 48 | Cole Simpson | Radford | 20 | Matthew Saunders | Radford | Radford High Stadium | ||||
| 2019 | 11/22 | 2A | Appomattox County | 21 | Doug Smith | Glenvar | 0 | Kevin Clifford | Appomattox | Bragg Stadium | ||||
| 2019 | 11/29 | 2A | Appomattox County | 35 | Doug Smith | Gretna | 14 | Cole Simpson | Appomattox | Bragg Stadium | ||||
| 2019 | 11/29 | 2A | Stuarts Draft | 14 | Nathan Floyd | East Rockingham | 7 | Donnie Coleman | Stuarts Draft | |||||
| 2019 | 11/29 | 2A | Thomas Jefferson R | 30 | P. J. Adams | King William | 28 | Dylan Dehart | Richmond | Huguenot High School | ||||
| 2019 | 11/30 | 2A | Graham | 43 | Tony Palmer | Central Wise | 14 | Luke Owens | Bluefield | Mitchell Stadium | ||||
| 2019 | 12/7 | 2A | Appomattox County | 28 | Doug Smith | Graham | 13 | Tony Palmer | Appomattox | Bragg Stadium | ||||
| 2019 | 12/7 | 2A | Stuarts Draft | 49 | Nathan Floyd | Thomas Jefferson R | 7 | P. J. Adams | Stuarts Draft | |||||
| 2019 | 12/14 | 2A | Appomattox County | 42 | Doug Smith | Stuarts Draft | 21 | Nathan Floyd | Salem | Salem Stadium | ||||
| 1,145 | 412 | |||||||||||||
| 36.94 | 13.29 | |||||||||||||