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1960 – Episcopal High School
1961 – Episcopal High School
1962 – Episcopal High School
1963 – Fork Union Military Academy
1964 – Woodberry Forest School
1965 – Woodberry Forest School
1966 – Fork Union Military Academy
1967 – Hargrave Military Academy
1968 – Woodberry Forest School
1969 – Episcopal High School
1970 – Episcopal High School
1971 – Hargrave Military Academy & Episcopal High School
1972 – St. Christopher’s School
1973 – Collegiate School
1974 – Bishop O’Connell High School
1975 – Bishop O’Connell High School
1976 – Bishop O’Connell High School
1977 – Bishop O’Connell High School
1978 – Fork Union Military Academy
1979 – Fork Union Military Academy
1980 – Woodberry Forest School
1981 – Fork Union Military Academy
1982 – Collegiate School
1983 – Bishop O’Connell High School
1984 – Bishop O’Connell High School
1985 – St. Christopher’s School
1986 – Woodberry Forest School
1987 – St. Christopher’s School
1988 – Fork Union Military Academy
1989 – Fork Union Military Academy
1990 – Fork Union Military Academy
1991 – Fork Union Military Academy
1992 – Fork Union Military Academy
1993 – Fork Union Military Academy
1994 – Fork Union Military Academy
1995 – Fork Union Military Academy
1996 – Fork Union Military Academy
1997 – Fork Union Military Academy
1998 – Fork Union Military Academy
1999 – Fork Union Military Academy
2000 – Fork Union Military Academy
2001 – Fork Union Military Academy
2002 – Fork Union Military Academy
2003 – Fork Union Military Academy
2004 – Fork Union Military Academy
2005 – Fork Union Military Academy
2006 – Fork Union Military Academy
2007 – Fork Union Military Academy
2008 – Fork Union Military Academy
2009 – St. Christopher’s School
2010 – Fork Union Military Academy
2011 – Liberty Christian Academy
2012 – Fork Union Military Academy
2013 – Woodberry Forest School

2014 – DI – Woodberry Forest School
2014 – DII – Broadwater Academy

2015 – DI – Woodberry Forest School
2015 – DII – Peninsula Catholic School

2016 – DI – Woodberry Forest School (RESULTS)
2016 – DII – Peninsula Catholic & Broadwater (RESULTS)

2017 – DI – St Christopher’s (RESULTS)
2017 – DII – Hampton Roads Academy (RESULTS)