Three-Time Individual Henlopen Champions
| Wrestler | Team | Years |
|---|---|---|
| Mark Bastianelli | Sussex Central | 1970-72 |
| Morgan Rigby | Caesar Rodney | 1972-74 |
| Bobby Bosco | Caesar Rodney | 1973-75 |
| Steve Bastianelli | Sussex Central | 1974-76 |
| Tyrone Gibbs | Cape Henlopen | 1974-76 |
| Orlando Pettyjohn | Milford | 1979-81 |
| David Leager | Smyrna | 1983, 1985-86 |
| Randy Smith | Caesar Rodney | 1983-85 |
| Randy Brown | Laurel/Delmar | 1984-85, 1987 |
| Rocky Jones | Dover | 1991-93 |
| Jason Moaney | Dover | 1992-94 |
| Mark Reynolds | Caesar Rodney | 2001-03 |
| Jon Hummel | Lake Forest/Milford | 2002-04 |
| Michael Crain | Smyrna | 2002-04 |
| Steve Billbrough | Caesar Rodney | 2002, 2004-05 |
| Ian Moser | Caesar Rodney | 2004-06 |
| Matt Cathell | Caesar Rodney | 2004-06 |
| Connor McDonald | Sussex Central | 2005-07 |
| Chris Diaz | Caesar Rodney | 2005-07 |
| Alex Meade | Caesar Rodney | 2005, 2007-08 |
| Alex Thomas | Sussex Tech | 2007-09 |
| Cody Broomall | Smyrna/Sussex Central | 2009-11 |
| Issah Meade | Caesar Rodney | 2009-11 |
| Micah Hight | Caesar Rodney | 2011-13 |
| Thomas Ott | Cape Henlopen | 2012-14 |
| Cameron Hayes | Caesar Rodney | 2016-18 |
| Tony Wuest | Smyrna | 2016-18 |
| Joe Natarcola | Smyrna | 2018-20 |
| Anthony Diaz | Milford | 2018-20 |
| Gabe Giampetro | Smyrna | 2019-20, 2022 |
| Jack Thode | Milford | 2019-20, 2022 |
| Trevor Copes | Caesar Rodney | 2023-25 |
| Patrick Donahue | Cape Henlopen | 2023-25 |