Three-Time Individual State Champions
| Wrestler | Team | Years |
|---|---|---|
| Buck Brinton | St. Andrews | 1958-60 |
| Skip Jones | Milford | 1960-62 |
| Steve Rhode | Tatnall | 1964-66 |
| Woody Thomas | De La Warr | 1965-67 |
| Jim Krapf | Tatnall | 1966-68 |
| Nick Episcopo | Dickinson | 1971-73 |
| Steve Bastianelli | Sussex Central | 1974-76 |
| Paul Collier | St. Marks | 1986-88 |
| Randy Smith | Caesar Rodney | 1983-85 |
| Paul Antonio | William Penn | 1989-91 |
| Tommy Davis | Salesianum | 1995-97 |
| Harry Blendt | Smyrna | 1996-98 |
| Gregg Quailes | William Penn | 1998-00 |
| Jordan Sianni | Hodgson | 1999-01 |
| Pat Atkinson | St. Marks | 2001-03 |
| Ian Moser | Caesar Rodney | 2004-06 |
| Matt Cathell | Caesar Rodney | 2004-06 |
| Andrew Bradley | St. Marks | 2004-06 |
| Connor McDonald | Sussex Central | 2005-07 |
| Nick Tiberi | Hodgson | 2006-08 |
| Alex Meade | Caesar Rodney | 2005, 2007-08 |
| Vinnie Ranauto | Caravel | 2006-08 |
| Sean Boylan | St. Marks | 2008-10 |
| Tyler Pendergast | St. Marks | 2009-11 |
| Cody Broomall | Smyrna/Sussex Central | 2009-11 |
| Issah Meade | Caesar Rodney | 2009-11 |
| Kaleb LeMaire | Caesar Rodney | 2010-12 |
| Micah Hight | Caesar Rodney | 2011-13 |
| Thomas Ott | Cape Henlopen | 2012-14 |
| Chase Archangelo | Smyrna | 2015-17 |
| Cameron Hayes | Milford/Caesar Rodney | 2015-16, 2018 |
| Tony Wuest | Smyrna | 2015, 2017-18 |
| Zach Spence | Salesianum | 2017-19 |
| Jackson Dean | Caesar Rodney | 2017, 2019-20 |
| Hugo Harp | Dover/Smyrna | 2018-20 |
| Kevin Hudson | Caesar Rodney | 2019-21 |
| Nicholas Hall | Caravel | 2019-20, 2022 |
| Jack Thode | Milford | 2020-22 |
| Justin Griffith | Sanford | 2021-23 |