| Year | Date | Opponent | Us | Them | Result | W | L | T | OT | Where | Location | Field | Coach | Notes | |
| 1995 | 11/3 | Bell County | 8 | 52 | L | 1 | Away | Log Mountain | Bill Musick | playoff at Log Mountain | |||||
| 1997 | 11/7 | Whitley County | 18 | 12 | W | 1 | Home | Paintsville | Eagle Stadium | Bill Musick | playoff at Paintsville | ||||
| 1997 | 11/14 | Bell County | 10 | 13 | L | 1 | Away | Log Mountain | Bill Musick | playoff at Log Mountain | |||||
| 1998 | 11/6 | Bell County | 6 | 22 | L | 1 | Away | Log Mountain | Bill Musick | playoff at Log Mountain | |||||
| 1999 | 11/5 | Madison Central | 55 | 63 | L | 1 | Away | Richmond | Bill Musick | playoff at Richmond | q | ||||
| 2000 | 11/3 | George Rogers Clark | 35 | 7 | W | 1 | Home | Paintsville | Eagle Stadium | Bill Musick | playoff at Paintsville | ||||
| 2000 | 11/10 | Tates Creek | 0 | 23 | L | 1 | Home | Paintsville | Eagle Stadium | Bill Musick | playoff at Paintsville | ||||
| 2005 | 11/4 | Madison Southern | 28 | 35 | L | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2006 | 11/3 | Boyd County | 50 | 6 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2006 | 11/10 | Paul Blazer | 28 | 21 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2006 | 11/17 | Rockcastle County | 29 | 7 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2006 | 11/24 | Covington Catholic | 14 | 38 | L | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2007 | 11/9 | Bryan Station | 48 | 27 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2007 | 11/16 | Montgomery County | 32 | 14 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2007 | 11/23 | Lincoln County | 22 | 43 | L | 1 | Away | Stanford | Jim Matney | playoff at Stanford | |||||
| 2008 | 11/14 | Holmes | 54 | 13 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2008 | 11/21 | Covington Catholic | 49 | 14 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2008 | 11/28 | Highlands | 21 | 35 | L | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2009 | 11/6 | Scott | 62 | 41 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2009 | 11/13 | Covington Catholic | 51 | 32 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2009 | 11/20 | Highlands | 21 | 42 | L | 1 | Away | Fort Thomas | David Cecil Memorial Stadium | Jim Matney | playoff at Fort Thomas | ||||
| 2010 | 11/5 | Scott | 47 | 13 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2010 | 11/12 | Covington Catholic | 41 | 28 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2010 | 11/19 | Highlands | 14 | 21 | L | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2011 | 11/4 | Holmes | 66 | 20 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2011 | 11/11 | Highlands | 20 | 67 | L | 1 | Away | Fort Thomas | David Cecil Memorial Stadium | Jim Matney | playoff at Fort Thomas | ||||
| 2012 | 11/2 | Harrison County | 68 | 14 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2012 | 11/9 | Covington Catholic | 15 | 45 | L | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2013 | 11/8 | Harrison County | 77 | 13 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2013 | 11/15 | Covington Catholic | 14 | 42 | L | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2014 | 11/7 | Harrison County | 67 | 14 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2014 | 11/14 | Covington Catholic | 7 | 19 | L | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2015 | 11/6 | Holmes | 41 | 0 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2015 | 11/13 | Greenup County | 49 | 6 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2015 | 11/20 | Scott | 27 | 26 | W | 1 | Away | Taylor Mill | Jim Matney | playoff at Taylor Mill | |||||
| 2015 | 11/27 | Wayne County | 21 | 14 | W | 1 | Away | Monticello | Jim Matney | playoff at Monticello | |||||
| 2015 | 12/6 | South Warren | 6 | 36 | L | 1 | Neutral | Bowling Green | L. T. Smith Stadium | Jim Matney | championship at Bowling Green | ||||
| 2016 | 11/4 | Scott | 54 | 7 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2016 | 11/11 | Greenup County | 55 | 8 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2016 | 11/18 | Paul Blazer | 51 | 0 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2016 | 11/25 | Wayne County | 51 | 0 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2016 | 12/4 | Franklin-Simpson | 48 | 0 | W | 1 | Neutral | Bowling Green | L. T. Smith Stadium | Jim Matney | championship at Bowling Green | ||||
| 2017 | 11/3 | Mason County | 43 | 0 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2017 | 11/10 | Scott | 64 | 16 | W | 1 | Away | Taylor Mill | Jim Matney | playoff at Taylor Mill | |||||
| 2017 | 11/17 | Paul Blazer | 54 | 27 | W | 1 | Away | Ashland | Putnam Stadium | Jim Matney | playoff at Ashland | ||||
| 2017 | 11/24 | Wayne County | 43 | 24 | W | 1 | Away | Monticello | Jim Matney | playoff at Monticello | |||||
| 2017 | 12/2 | Franklin-Simpson | 21 | 35 | L | 1 | Neutral | Lexington | Kroger Field | Jim Matney | championship at Lexington | ||||
| 2018 | 11/2 | Bourbon County | 55 | 7 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2018 | 11/9 | Scott | 50 | 7 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2018 | 11/16 | Paul Blazer | 50 | 14 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2018 | 11/23 | Knox Central | 59 | 20 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2018 | 12/1 | Franklin-Simpson | 12 | 14 | L | 1 | Neutral | Lexington | Kroger Field | Jim Matney | championship at Lexington | ||||
| 2019 | 11/8 | Letcher County Central | 49 | 7 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2019 | 11/15 | Harlan County | 50 | 6 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2019 | 11/22 | Wayne County | 36 | 7 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2019 | 11/29 | Madisonville-North Hopkins | 52 | 14 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2019 | 12/7 | Boyle County | 21 | 20 | W | 1 | Neutral | Lexington | Kroger Field | Jim Matney | championship at Lexington | ||||
| 2020 | 11/20 | Harlan County | 46 | 8 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2020 | 11/27 | Letcher County Central | 50 | 0 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2020 | 12/4 | Corbin | 28 | 14 | W | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2020 | 12/11 | Franklin County | 12 | 20 | L | 1 | Home | Paintsville | Eagle Stadium | Jim Matney | playoff at Paintsville | ||||
| 2021 | 11/5 | Clay County | 56 | 7 | W | 1 | Home | Paintsville | Coach Jim Matney Field | Steve Trimble | playoff at Paintsville | ||||
| 2021 | 11/12 | Letcher County Central | 50 | 14 | W | 1 | Home | Paintsville | Coach Jim Matney Field | Steve Trimble | playoff at Paintsville | ||||
| 2021 | 11/19 | Corbin | 34 | 13 | W | 1 | Away | Corbin | Campbell Field | Steve Trimble | playoff at Corbin | ||||
| 2021 | 11/26 | Franklin County | 42 | 24 | W | 1 | Home | Paintsville | Coach Jim Matney Field | Steve Trimble | playoff at Paintsville | ||||
| 2021 | 12/3 | Boyle County | 13 | 30 | L | 1 | Neutral | Lexington | Kroger Field | Steve Trimble | championship at Lexington | ||||
| 2022 | 11/4 | Lincoln County | 36 | 7 | W | 1 | Home | Paintsville | Coach Jim Matney Field | Jesse Peck | playoff at Paintsville | ||||
| 2022 | 11/11 | Wayne County | 43 | 6 | W | 1 | Home | Paintsville | Coach Jim Matney Field | Jesse Peck | playoff at Paintsville | ||||
| 2022 | 11/18 | Corbin | 21 | 35 | L | 1 | Away | Corbin | Campbell Field | Jesse Peck | playoff at Corbin | ||||
| 2023 | 11/3 | Grant County | 54 | 14 | W | 1 | Home | Paintsville | Coach Jim Matney Field | Jesse Peck | playoff at Paintsville | ||||
| 2023 | 11/10 | Boyd County | 28 | 14 | W | 1 | Home | Paintsville | Coach Jim Matney Field | Jesse Peck | playoff at Paintsville | ||||
| 2023 | 11/17 | Covington Catholic | 0 | 31 | L | 1 | Away | Covington | Wooten Field | Jesse Peck | playoff at Covington | ||||
| 2024 | 11/8 | Grant County | 49 | 7 | W | 1 | Home | Paintsville | Coach Jim Matney Field | Jesse Peck | playoff at Paintsville | ||||
| 2024 | 11/15 | Covington Catholic | 13 | 14 | L | 1 | Away | Covington | Wooten Field | Jesse Peck | playoff at Covington | ||||
| 2025 | 11/6 | Harrison County | 48 | 16 | W | 1 | Home | Paintsville | Coach Jim Matney Field | Jesse Peck | playoff at Paintsville | ||||
| 2025 | 11/14 | Covington Catholic | 29 | 36 | L | 1 | Home | Paintsville | Coach Jim Matney Field | Jesse Peck | playoff at Paintsville | ||||
| 2,791 | 1,481 | 52 | 24 | 0 | .684 | ||||||||||
| 36.72 | 19.49 | 17.24 |