Four-Time Individual Henlopen Individual Champions

There have been only 10 Four-Time Henlopen conference champions since 1965.

Wrestler	Team	Years
Kirk Rogers	Sussex Central	1989-93
Harry Blendt	Smyrna	1995-98
Will Saylor	Indian River/Laurel	2001-04
Brandon Shultie	Sussex Central	2007-10
Codey Combs	Sussex Central	2008-11
Kaleb LeMaire	Caesar Rodney	2009-12
Brent Fleetwood	Smyrna	2011-14
Jackson Dean	Caesar Rodney	2017-20
Malachi Stratton	Sussex Central	2022-25
Nicolas Walker	Cape Henlopen	2023-26