| Year | Date | Opponent | Us | Them | Result | W | L | T | OT | Place | Location | Field | Coach | Notes |
| 1966 | 9/10 | Madison Central | 35 | 0 | W | 1 | Away | Richmond | Don Netoskie | |||||
| 1967 | 9/8 | Madison Central | 20 | 6 | W | 1 | Home | Winchester | Cardinal Stadium | Lloyd Hodge | ||||
| 1968 | 9/13 | Madison Central | 20 | 0 | W | 1 | Away | Richmond | Lloyd Hodge | |||||
| 1969 | 9/12 | Madison Central | 43 | 6 | W | 1 | Home | Winchester | Cardinal Stadium | Lloyd Hodge | ||||
| 1970 | 9/11 | Madison Central | 20 | 6 | W | 1 | Away | Richmond | Lloyd Hodge | |||||
| 1971 | 9/10 | Madison Central | 0 | 0 | T | 1 | Home | Winchester | Cardinal Stadium | Lloyd Hodge | ||||
| 1972 | 9/8 | Madison Central | 15 | 6 | W | 1 | Away | Richmond | Lloyd Hodge | |||||
| 1973 | 9/7 | Madison Central | 6 | 36 | L | 1 | Home | Winchester | Cardinal Stadium | Bill Urbanic | ||||
| 1974 | 9/13 | Madison Central | 15 | 6 | W | 1 | Away | Richmond | Don Danko | |||||
| 1975 | 9/12 | Madison Central | 27 | 8 | W | 1 | Home | Winchester | Cardinal Stadium | Don Danko | ||||
| 1976 | 9/10 | Madison Central | 13 | 14 | L | 1 | 1OT | Away | Richmond | Don Danko | ||||
| 1977 | 9/9 | Madison Central | 8 | 14 | L | 1 | Home | Winchester | Cardinal Stadium | Don Danko | ||||
| 1978 | 9/8 | Madison Central | 14 | 13 | W | 1 | Away | Richmond | Don Danko | |||||
| 1979 | 9/7 | Madison Central | 7 | 0 | W | 1 | Home | Winchester | Cardinal Stadium | Don Danko | ||||
| 1980 | 9/12 | Madison Central | 16 | 24 | L | 1 | Away | Richmond | Don Danko | |||||
| 1981 | 9/25 | Madison Central | 6 | 13 | L | 1 | Home | Winchester | Cardinal Stadium | Don Danko | ||||
| 1982 | 9/24 | Madison Central | 20 | 14 | W | 1 | Away | Richmond | Don Danko | |||||
| 1983 | 9/23 | Madison Central | 14 | 7 | W | 1 | Home | Winchester | Cardinal Stadium | Don Danko | ||||
| 1984 | 10/12 | Madison Central | 19 | 35 | L | 1 | Away | Richmond | Don Danko | |||||
| 1985 | 10/18 | Madison Central | 20 | 14 | W | 1 | Home | Winchester | Cardinal Stadium | Don Danko | ||||
| 1986 | 10/16 | Madison Central | 21 | 18 | W | 1 | Away | Richmond | Don Danko | |||||
| 1987 | 10/16 | Madison Central | 9 | 0 | W | 1 | Home | Winchester | Cardinal Stadium | Don Danko | ||||
| 1988 | 10/14 | Madison Central | 35 | 28 | W | 1 | Away | Richmond | Don Danko | |||||
| 1989 | 10/13 | Madison Central | 24 | 28 | L | 1 | Home | Winchester | Cardinal Stadium | Don Danko | ||||
| 1990 | 10/12 | Madison Central | 14 | 15 | L | 1 | Away | Richmond | Don Danko | |||||
| 1991 | 10/18 | Madison Central | 44 | 11 | W | 1 | Home | Winchester | Cardinal Stadium | Don Danko | ||||
| 1991 | 11/22 | Madison Central | 41 | 13 | W | 1 | Home | Winchester | Cardinal Stadium | Don Danko | playoff at Winchester | |||
| 1992 | 10/16 | Madison Central | 32 | 14 | W | 1 | Away | Richmond | Don Danko | |||||
| 1993 | 10/15 | Madison Central | 22 | 0 | W | 1 | Home | Winchester | Cardinal Stadium | Don Danko | ||||
| 1994 | 10/14 | Madison Central | 7 | 21 | L | 1 | Away | Richmond | Don Danko | |||||
| 1995 | 8/25 | Madison Central | 10 | 26 | L | 1 | Home | Winchester | Cardinal Stadium | Don Danko | ||||
| 1996 | 8/30 | Madison Central | 0 | 48 | L | 1 | Away | Richmond | Don Danko | |||||
| 1997 | 8/29 | Madison Central | 6 | 41 | L | 1 | Home | Winchester | Cardinal Stadium | Don Danko | ||||
| 1998 | 8/28 | Madison Central | 14 | 42 | L | 1 | Away | Richmond | Steve Ely | |||||
| 1999 | 10/22 | Madison Central | 20 | 40 | L | 1 | Away | Richmond | Paul Columbia | |||||
| 2000 | 10/20 | Madison Central | 3 | 17 | L | 1 | Home | Winchester | Cardinal Stadium | Paul Columbia | ||||
| 2001 | 9/28 | Madison Central | 31 | 20 | W | 1 | Away | Richmond | Paul Columbia | |||||
| 2002 | 10/4 | Madison Central | 3 | 25 | L | 1 | Home | Winchester | Cardinal Stadium | Paul Columbia | ||||
| 2003 | 10/17 | Madison Central | 10 | 54 | L | 1 | Away | Richmond | Paul Columbia | |||||
| 2004 | 10/15 | Madison Central | 6 | 14 | L | 1 | Home | Winchester | Cardinal Stadium | Paul Columbia | ||||
| 2005 | 10/14 | Madison Central | 13 | 44 | L | 1 | Away | Richmond | Paul Columbia | |||||
| 2006 | 10/13 | Madison Central | 14 | 35 | L | 1 | Home | Winchester | Cardinal Stadium | Paul Columbia | ||||
| 2007 | 9/21 | Madison Central | 26 | 45 | L | 1 | Away | Richmond | Paul Columbia | |||||
| 2007 | 11/9 | Madison Central | 14 | 27 | L | 1 | Away | Richmond | Paul Columbia | playoff at Richmond | ||||
| 2008 | 9/26 | Madison Central | 35 | 49 | L | 1 | Home | Winchester | Cardinal Stadium | Paul Columbia | ||||
| 2009 | 10/23 | Madison Central | 34 | 17 | W | 1 | Away | Richmond | Paul Columbia | |||||
| 2010 | 10/22 | Madison Central | 35 | 14 | W | 1 | Home | Winchester | Cardinal Stadium | Paul Columbia | ||||
| 2011 | 10/21 | Madison Central | 13 | 15 | L | 1 | Away | Richmond | Paul Columbia | |||||
| 2012 | 10/19 | Madison Central | 18 | 50 | L | 1 | Home | Winchester | Cardinal Stadium | Steven Collins | ||||
| 2013 | 10/25 | Madison Central | 30 | 32 | L | 1 | Away | Richmond | Steven Collins | |||||
| 2014 | 10/24 | Madison Central | 46 | 33 | W | 1 | Home | Winchester | Cardinal Stadium | Mike Riddle | ||||
| 2015 | 10/23 | Madison Central | 7 | 38 | L | 1 | Home | Winchester | Cardinal Stadium | Mike Riddle | ||||
| 2016 | 10/21 | Madison Central | 6 | 49 | L | 1 | Away | Richmond | Oliver Lucas | |||||
| 2017 | 10/20 | Madison Central | 14 | 34 | L | 1 | Home | Winchester | Cardinal Stadium | Oliver Lucas | ||||
| 2018 | 10/19 | Madison Central | 7 | 31 | L | 1 | Away | Richmond | Oliver Lucas | |||||
| 2019 | 10/18 | Madison Central | 42 | 34 | W | 1 | Home | Winchester | Cardinal Stadium | Oliver Lucas | ||||
| 2019 | 11/8 | Madison Central | 35 | 20 | W | 1 | Home | Winchester | Cardinal Stadium | Oliver Lucas | playoff at Winchester | |||
| 2020 | 10/16 | Madison Central | 48 | 15 | W | 1 | Away | Richmond | Oliver Lucas | |||||
| 2021 | 10/15 | Madison Central | 7 | 43 | L | 1 | Home | Winchester | Cardinal Stadium | Oliver Lucas | ||||
| 2022 | 10/14 | Madison Central | 14 | 27 | L | 1 | Away | Richmond | Joe Chirico | |||||
| 2023 | 10/13 | Madison Central | 13 | 16 | L | 1 | Home | Winchester | Cardinal Stadium | Joe Chirico | ||||
| 2024 | 10/18 | Madison Central | 27 | 15 | W | 1 | Away | Richmond | Joe Chirico | |||||
| 2025 | 10/17 | Madison Central | 0 | 49 | L | 1 | Home | Winchester | Cardinal Stadium | Joe Chirico | ||||
| 2025 | 11/14 | Madison Central | 7 | 45 | L | 1 | Home | Winchester | Cardinal Stadium | Joe Chirico | playoff at Lexington | |||
| 2026 | 10/16 | Madison Central | Away | Richmond | Dane Damron | |||||||||
| 1,195 | 1,474 | 28 | 35 | 1 | .445 | |||||||||
| 18.67 | 23.03 | -4.36 |