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City-County Championship
| Year | Champion | Co-Champion | Co-Champion |
| 1971 | OHS | ||
| 1972 | OHS | ||
| 1973 | OHS | Catholic | |
| 1974 | OHS | ||
| 1975 | OHS | ||
| 1976 | Catholic | ||
| 1977 | OHS | ||
| 1978 | Apollo | Catholic | |
| 1979 | OHS | ||
| 1980 | OHS | ||
| 1981 | OHS | Catholic | |
| 1982 | OHS | ||
| 1983 | OHS | ||
| 1984 | OHS | Catholic | Daviess Co |
| 1985 | OHS | ||
| 1986 | OHS | ||
| 1987 | Apollo | ||
| 1988 | Apollo | ||
| 1989 | Daviess Co | ||
| 1990 | OHS | ||
| 1991 | OHS | ||
| 1992 | OHS | ||
| 1993 | OHS | ||
| 1994 | OHS | ||
| 1995 | Apollo | ||
| 1996 | Daviess Co | ||
| 1997 | Apollo | ||
| 1998 | Apollo | ||
| 1999 | OHS | ||
| 2000 | OHS | ||
| 2001 | OHS | ||
| 2002 | Catholic | ||
| 2003 | Catholic | ||
| 2004 | Apollo | ||
| 2005 | OHS | ||
| 2006 | OHS | ||
| 2007 | OHS | ||
| 2008 | OHS | ||
| 2009 | OHS | ||
| 2010 | OHS | ||
| 2011 | Catholic | ||
| 2012 | Catholic | ||
| 2013 | OHS | ||
| 2014 | OHS | ||
| 2015 | OHS | ||
| 2016 | Catholic | ||
| 2017 | DC | Apollo | Catholic |
| 2018 | OHS | Catholic | DC |
| 2019 | OHS | ||
| 2020 | OHS | ||
| 2021 | OHS |
| Overall | Out right | ||
| Champs | Champs | Ties | |
| OHS | 35 | 31 | 3 |
| Catholic | 10 | 6 | 4 |
| Daviess Co | 3 | 2 | 1 |
| Apollo | 7 | 6 | 1 |
