| Year | Location |
| 2009 | Camden-Wyoming (District 1) |
| 2008 | Lewes (District 3) |
| 2007 | Naamans (Wilmington) (District 2) |
| 2006 | Dover (District 1) |
| 2005 | Nanticoke (Seaford) (District 3) |
| 2004 | Newark American (District 2) |
| 2003 | Smyrna-Clayton (District 1) |
| 2002 | Nanticoke (Seaford) (District 3) |
| 2001 | Midway (Wilmington) (District 2) |
| 2000 | Middletown-Odessa-Townsend (District 1) |
| 1999 | Georgetown (District 3) |
| 1998 | Midway (Wilmington) (District 2) |
| 1997 | Smyrna-Clayton (District 1) |
| 1996 | Nanticoke (Seaford) (District 3) |
| 1995 | Newark National (District 2) |
| 1994 | Marydel (District 1) |
| 1993 | Newark American (District 2) |
| 1992 | Camden-Wyoming (District 1) |
| 1991 | Newark National (District 2) |
| 1990 | Nanticoke (Seaford) (District 1) |
| 1989 | Piedmont (Hockessin) (District 2) |
| 1988 | Middletown-Odessa-Townsend (District 1) |
| 1987 | Stanton-Newport (District 2) |
| 1986 | Middletown-Odessa-Townsend (District 1) |
| 1985 | Newark American (District 2) |
| 1984 | Middletown-Odessa-Townsend (District 1) |
| 1983 | Newark National (District 2) |
| 1982 | Nanticoke (Seaford) (District 1) |
| 1981 | Claymont (District 2) |
| 1980 | Smyrna-Clayton (District 1) |
| 1979 | Newark American (District 2) |
| 1978 | Smyrna-Clayton (District 1) |
| 1977 | Newark (District 2) |
| 1976 | Georgetown (District 1) |
| 1975 | New Castle (District 2) |
| 1974 | Smyrna-Clayton (District 1) |
| 1973 | New Castle (District 2) |
| 1972 | Camden-Wyoming (District 1) |
| 1971 | Newark (District 2) |
| 1970 | Camden-Wyoming (District 1) |
| 1969 | Naamans (Wilmington) (District 2) |
| 1968 | Camden-Wyoming (District 1) |
| 1967 | Newark National (District 2) |
| 1966 | Rehoboth Beach (District 1) |
| 1965 | New Castle (District 2) |
| 1964 | Middletown-Odessa-Townsend (District 1) |
| 1963 | Dover (District 1) |
| 1962 | Georgetown (District 1) |
| 1961 | Middletown-Odessa-Townsend (District 1) |
| 1960 | Nanticoke (Seaford) (District 1) |
| 1959 | Nanticoke (Seaford) (District 1) |
| 1958 | Wilmington Optimist (District 1) |
| 1957 | Newark National (District 1) |