| Year | Coach-of-the-Year | School | Asst. Coach-of-the-Year | School |
| 1978 | Tom Leonard | Dover Air Base H.S. | ||
| 1979 | Tom Nash | Middletown H.S. | ||
| 1980 | Frank Aiello | St. Elizabeth's H.S. | ||
| 1981 | Bob Colburn Jim Hudson |
St. Andrew's School Sussex Central H.S. |
||
| 1982 | Father Robert Kenney | Salesianum School | ||
| 1983 | Frank Aiello | St. Elizabeth's H.S. | ||
| 1984 | Steve Hyde | Tower Hill School | ||
| 1985 | Bill Falasco |
Lake Forest H.S. St. Mark's H.S. |
||
| 1986 | Richard Green | Middletown H.S. | ||
| 1987 | Steve Hyde | Tower Hill School | ||
| 1988 | Bob Colburn Paul Niggebrugge |
St. Andrew's School Caravel Academy |
||
| 1989 | Woody Long | Sussex Central H.S. | ||
| 1990 | Tom Beddow | St. Elizabeth's H.S. | ||
| 1991 | Bob Colburn | St. Andrew's School | ||
| 1992 | John Newman | Caesar Rodney H.S. | ||
| 1993 | Tom Beddow Tom Pegelow |
St. Elizabeth's H.S. Seaford H.S. |
||
| 19942 | Rob Limmina Tom Pegelow |
Mt. Pleasant H.S. Seaford H.S. |
||
| 1995 | Bill Falasco | Lake Forest H.S. | ||
| 1996 | Derek Prillaman | Smyrna H.S. | ||
| 1997 | Larry Wheeler | Brandywine H.S. | ||
| 1998 | Jerry Mears | Laurel H.S. | ||
| 1999 | Matt Smith | St. Mark's H.S. | Soddy Limmina | Mt. Pleasant H.S. |
| 2000 | Dennis Walker | Salesianum School | Larry Walker | St. Andrew's School |
| 2001 | Curt Bedford | Newark H.S. | Richard Green | Howard VoTech |
| 2002 | Ralph Cicconi Bob Colburn |
Hodgson VoTech St. Andrew's School |
Don Krug | Caravel Academy |
| 2003 | Tom Beddow | St. Elizabeth's H.S. | Mark Pruitt | McKean H.S. |
| 2004 | John Newman | Caesar Rodney H.S. | Tim Hamberger John Wilson |
Brandywine H.S. St. Mark's H.S. |
| 2005 | George Eilers | Polytech H.S. | Mike Peden | Salesianum School |
| 2006 | Ken Cummings Doug Nowell |
Seaford H.S. Salesianum School |
Scott Hitchens | Sussex Central H.S. |
| 2007 | Darren Brodie Chris Moxley John Nichols |
A.I.duPont H.S. Hodgson Vo-Tech Milford H.S. |
Steve Lepre | William Penn H.S. |