| Year | Date | Opponent | Us | Them | Result | W | L | T | OT | Where | Location | Field | Coach | Notes |
| 1965 | 11/12 | Belfry | 21 | 19 | W | 1 | Home | Middlesboro | Bradner Stadium | Walt Green | playoff at Middlesboro | |||
| 1965 | 11/20 | Newport Catholic | 18 | 6 | W | 1 | Away | Newport | Newport Public Stadium | Walt Green | playoff at Newport | |||
| 1965 | 11/27 | Hopkinsville | 6 | 24 | L | 1 | Neutral | Lexington | Stoll Field | Walt Green | championship at Lexington | |||
| 1970 | 11/13 | Hazard | 0 | 12 | L | 1 | Away | Hazard | Collins Field | Tom Stapleton | playoff at Hazard | |||
| 1971 | 11/12 | Hazard | 22 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Tom Stapleton | playoff at Middlesboro | |||
| 1971 | 11/19 | Bryan Station | 8 | 18 | L | 1 | Away | Lexington | Tom Stapleton | playoff at Lexington | ||||
| 1972 | 11/10 | Paul Blazer | 14 | 33 | L | 1 | Away | Ashland | Putnam Stadium | Tom Stapleton | playoff at Ashland | |||
| 1974 | 11/15 | Boyd County | 28 | 14 | W | 1 | Away | Canonsburg | Tom Stapleton | playoff at Canonsburg | ||||
| 1974 | 11/22 | Henry Clay | 14 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Tom Stapleton | playoff at Middlesboro | |||
| 1974 | 11/29 | Owensboro | 7 | 14 | L | 1 | Neutral | Richmond | Hanger Stadium | Tom Stapleton | championship at Richmond | |||
| 1975 | 11/14 | Somerset | 35 | 6 | W | 1 | Away | Somerset | William Clark Field | Tom Stapleton | playoff at Somerset | |||
| 1975 | 11/21 | Rowan County | 41 | 12 | W | 1 | Home | Middlesboro | Bradner Stadium | Tom Stapleton | playoff at Middlesboro | |||
| 1975 | 11/28 | Scott County | 20 | 22 | L | 1 | Neutral | Bowling Green | Tom Stapleton | championship at Bowling Green | ||||
| 1978 | 11/10 | Somerset | 0 | 31 | L | 1 | Home | Middlesboro | Bradner Stadium | Tom Stapleton | playoff at Middlesboro | |||
| 1981 | 11/13 | Somerset | 14 | 15 | L | 1 | Away | Somerset | William Clark Field | Ed Vanhoose | playoff at Somerset | |||
| 1991 | 11/8 | Anderson County | 19 | 22 | L | 1 | Home | Middlesboro | Bradner Stadium | Gary Barnett | playoff at Middlesboro | |||
| 1992 | 11/6 | Danville | 0 | 42 | L | 1 | Away | Danville | Admiral Stadium | Gary Barnett | playoff at Danville | |||
| 1994 | 11/4 | Bourbon County | 36 | 25 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1994 | 11/11 | Boyle County | 0 | 40 | L | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1995 | 11/3 | Phelps | 40 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1995 | 11/10 | Hazard | 49 | 14 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1995 | 11/18 | Pikeville | 7 | 42 | L | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1996 | 11/8 | Fleming-Neon | 42 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1996 | 11/15 | Pikeville | 18 | 33 | L | 1 | Away | Pikeville | W. C. Hambley Athletic Complex | Ken Roark | playoff at Pikeville | |||
| 1997 | 11/7 | Elkhorn City | 54 | 16 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1997 | 11/14 | Cumberland | 36 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1997 | 11/21 | Lynn Camp | 27 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1997 | 11/28 | Beechwood | 13 | 34 | L | 1 | Away | Beechwood | Edgar McNabb Field | Ken Roark | playoff at Beechwood | |||
| 1998 | 11/6 | South Floyd | 49 | 8 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1998 | 11/13 | Hazard | 50 | 12 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1998 | 11/20 | Pikeville | 78 | 34 | W | 1 | Away | Pikeville | W. C. Hambley Athletic Complex | Ken Roark | playoff at Pikeville | |||
| 1998 | 11/27 | Beechwood | 29 | 13 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1998 | 12/4 | Mayfield | 27 | 6 | W | 1 | Neutral | Louisville | Cardinal Stadium | Ken Roark | championship at Louisville | |||
| 1999 | 11/5 | Whitesburg | 41 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1999 | 11/12 | Leslie County | 43 | 20 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1999 | 11/19 | Breathitt County | 44 | 37 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 1999 | 11/26 | Boyle County | 14 | 66 | L | 1 | Away | Danville | Ballard L. Robinson Field | Ken Roark | playoff at Danville | |||
| 2000 | 11/3 | Whitesburg | 37 | 21 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2000 | 11/10 | Prestonsburg | 7 | 30 | L | 1 | Away | Prestonsburg | Ken Roark | playoff at Prestonsburg | ||||
| 2001 | 11/2 | Pikeville | 56 | 41 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2001 | 11/9 | Paintsville | 23 | 28 | L | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2002 | 11/8 | Phelps | 58 | 8 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2002 | 11/15 | Paintsville | 35 | 8 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2002 | 11/22 | Pikeville | 25 | 13 | W | 1 | Away | Pikeville | W. C. Hambley Athletic Complex | Ken Roark | playoff at Pikeville | |||
| 2002 | 11/29 | Beechwood | 14 | 37 | L | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2003 | 11/7 | Shelby Valley | 55 | 14 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2003 | 11/14 | Sheldon Clark | 26 | 14 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2003 | 11/21 | Belfry | 0 | 21 | L | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2004 | 11/5 | Pike County Central | 50 | 16 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2004 | 11/12 | Belfry | 7 | 49 | L | 1 | Away | Belfry | Al Vipperman Stadium | Ken Roark | playoff at Belfry | |||
| 2005 | 11/4 | Prestonsburg | 40 | 20 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Prestonsburg | |||
| 2005 | 11/11 | Belfry | 21 | 42 | L | 1 | Away | Belfry | Al Vipperman Stadium | Ken Roark | playoff at Belfry | |||
| 2006 | 11/3 | Cawood | 49 | 13 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2006 | 11/10 | Leslie County | 21 | 13 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2006 | 11/17 | Belfry | 26 | 49 | L | 1 | Away | Belfry | Al Vipperman Stadium | Ken Roark | playoff at Belfry | |||
| 2007 | 11/9 | Leslie County | 48 | 6 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2007 | 11/16 | Corbin | 13 | 28 | L | 1 | Away | Corbin | Campbell Field | Ken Roark | playoff at Corbin | |||
| 2008 | 11/14 | Shelby Valley | 35 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2008 | 11/21 | Prestonsburg | 7 | 20 | L | 1 | Away | Prestonsburg | Josh Francis Field | Ken Roark | playoff at Prestonsburg | |||
| 2009 | 11/6 | Bath County | 49 | 14 | W | 1 | Home | Middlesboro | Bradner Stadium | Ken Roark | playoff at Middlesboro | |||
| 2009 | 11/13 | Prestonsburg | 20 | 61 | L | 1 | Away | Prestonsburg | Josh Francis Field | Ken Roark | playoff at Prestonsburg | |||
| 2010 | 11/5 | Morgan County | 47 | 8 | W | 1 | Home | Middlesboro | Bradner Stadium | Randy Frazier | playoff at Middlesboro | |||
| 2010 | 11/12 | Prestonsburg | 6 | 40 | L | 1 | Away | Prestonsburg | Josh Francis Field | Randy Frazier | playoff at Prestonsburg | |||
| 2011 | 11/4 | Leslie County | 12 | 35 | L | 1 | Away | Hyden | Randy Frazier | playoff at Hyden | ||||
| 2012 | 11/2 | Prestonsburg | 33 | 36 | L | 1 | Away | Prestonsburg | Josh Francis Field | Randy Frazier | playoff at Prestonsburg | |||
| 2013 | 11/8 | Leslie County | 44 | 28 | W | 1 | Home | Middlesboro | Bradner Stadium | Randy Frazier | playoff at Middlesboro | |||
| 2013 | 11/15 | Somerset | 13 | 19 | L | 1 | 1OT | Home | Middlesboro | Bradner Stadium | Randy Frazier | playoff at Middlesboro | ||
| 2014 | 11/7 | Prestonsburg | 7 | 29 | L | 1 | Away | Prestonsburg | Josh Francis Field | Zach Massengill | playoff at Prestonsburg | |||
| 2015 | 11/6 | Shelby Valley | 13 | 56 | L | 1 | Away | Robinson Creek | Teco Field | Zach Massengill | playoff at Robinson Creek | |||
| 2016 | 11/4 | Leslie County | 26 | 44 | L | 1 | Away | Hyden | Zach Massengill | playoff at Hyden | ||||
| 2017 | 11/3 | Prestonsburg | 14 | 35 | L | 1 | Away | Prestonsburg | Josh Francis Field | Zach Massengill | playoff at Prestonsburg | |||
| 2019 | 11/8 | Leslie County | 57 | 22 | W | 1 | Home | Middlesboro | Bradner Stadium | Larry French | playoff at Middlesboro | |||
| 2019 | 11/15 | Breathitt County | 15 | 50 | L | 1 | Away | Jackson | Mike Holcomb Athletic Complex | Larry French | playoff at Jackson | |||
| 2021 | 11/5 | Leslie County | 46 | 0 | W | 1 | Home | Middlesboro | Bradner Stadium | Larry French | playoff at Middlesboro | |||
| 2021 | 11/12 | Breathitt County | 43 | 33 | W | 1 | Home | Middlesboro | Bradner Stadium | Larry French | playoff at Middlesboro | |||
| 2021 | 11/19 | West Carter | 33 | 6 | W | 1 | Home | Middlesboro | Bradner Stadium | Larry French | playoff at Middlesboro | |||
| 2021 | 11/26 | Lexington Christian | 0 | 58 | L | 1 | Away | Lexington | Larry French | playoff at Lexington | ||||
| 2022 | 11/4 | Prestonsburg | 42 | 30 | W | 1 | Home | Middlesboro | Bradner Stadium | Larry French | playoff at Middlesboro | |||
| 2022 | 11/11 | Shelby Valley | 21 | 28 | L | 1 | Away | Robinson Creek | Teco Field | Larry French | playoff at Robinson Creek | |||
| 2023 | 11/2 | Lynn Camp | 51 | 8 | W | 1 | Home | Middlesboro | Bradner Stadium | Larry French | playoff at Middlesboro | |||
| 2023 | 11/10 | Paintsville | 40 | 14 | W | 1 | Home | Middlesboro | Bradner Stadium | Larry French | playoff at Middlesboro | |||
| 2023 | 11/17 | Pikeville | 14 | 34 | L | 1 | Away | Pikeville | W. C. Hambley Athletic Complex | Larry French | playoff at Pikeville | |||
| 2024 | 11/8 | Paintsville | 19 | 32 | L | 1 | Home | Middlesboro | Bradner Stadium | Larry French | playoff at Middlesboro | |||
| 2025 | 11/7 | Harlan | 56 | 6 | W | 1 | Home | Middlesboro | Bradner Stadium | Larry French | playoff at Middlesboro | |||
| 2025 | 11/14 | Hazard | 44 | 36 | W | 1 | Home | Middlesboro | Bradner Stadium | Larry French | playoff at Middlesboro | |||
| 2025 | 11/21 | Pikeville | 14 | 42 | L | 1 | Away | Pikeville | W. C. Hambley Athletic Complex | Larry French | playoff at Pikeville | |||
| 2,396 | 1,985 | 47 | 39 | 0 | .547 | |||||||||
| 27.86 | 23.08 | 4.78 | ||||||||||||