| Year |
Division One - Coach |
Division Two - Coach |
| 1993 |
William Penn- Jack Holloway |
Smyrna - Mike Dulin |
| 1994 |
William Penn - Jack Holloway |
Smyrna - Mike Dulin |
| 1995 |
St. Marks - Steve Bastianelli |
A.I. duPont - George Lacsny |
| 1996 |
William Penn - Jack Holloway |
Smyrna - Mike Dulin |
| 1997 |
St. Marks - Steve Bastianelli |
Hodgson - Jerry Lamey |
| 1998 |
St. Marks - Steve Bastianelli |
Hodgson - Jerry Lamey |
| 1999 |
St. Marks - Steve Bastianelli |
Hodgson - Jerry Lamey |
| 2000 |
William Penn - Jack Holloway |
Hodgson - Jerry Lamey |
| 2001 |
Caesar Rodney - Dicky Howell |
Hodgson - Jerry Lamey |
| 2002 |
St. Marks - Steve Bastianello |
Hodgson - Jerry Lamey |
| 2003 |
Caesar Rodney - Dicky Howell |
Smyrna - |
