Highland High School
St. Paul High School
| 1946 | 1947 | 1948 | 1949 | 1950 |
| 1951 | 1952 | 1953 | 1954 | 1955 |
| 1956 | 1957 | 1958 | 1959 | 1960 |
| 1961 | 1962 | 1963 | 1964 | 1965 |
| 1966 | 1967 | 1968 | 1969 | 1970 |
| 1971 | 1972 | 1973 | 1974 | 1975 |
| 1976 | 1977 | 1978 | 1979 | 1980 |
| 1981 | 1982 | 1983 | 1984 | 1985 |
| 1986 | ||||
PORTA High School – Petersburg, IL
| 1984 | 1985 | 1986 | 1987 | |
Harris High School – Petersburg, IL
| 1965 | 1964 | 1963 | 1962 | 1961 |
| 1960 |
Tallula High School – Tallula, IL
| 1963 | 1962 | 1961 | 1960 | 1958 |
| 1957 | 1956 | 1955 |
Highland Middle School
| 2001 | 2004 | 2005 | 2006 | 2007 |
| 2009 | 2010 | 2011 | 2012 | 2013 |
| 2014 | 2015 |
Highland Primary & Elementary
| 1983 | 1985 | 1986 | 1987 | 1988 |
| 1989 | 1990 | 1991 | 1992 | 1993 |
| 1994 | 1995 | 1996 | 1997 | 1998 |
| 1999 | 2000 | 2001 | 2002 | 2003 |
| 2004 | 2005 | 2006 | 2007 | 2008 |
| 2009 | 2010 | 2011 | 2012 | 2013 |
| 2014 | 2015 | 2017 | 2018 | 2019 |
| 2020 | 2021 |
Highland High School Alumni
| 1994 | 1999 | 2007 | ||
Evangelical United Church of Christ
| 1963-1965 | 1975 |
| 1981 | 1990 |
| 1994 | 2000 |
| 2005 | 2009 |
| 2015 |
St. Paul Catholic Church
| 1991 | 1996 | 2001 | ||
| 2006 | 2011 |