Four-Time Individual State Champions
| Wrestler | Team | Years |
|---|---|---|
| Jim Terry | St. Andrews | 1957-60 |
| Kurt Howell | Newark | 1983-86 |
| Randy Brown | Laurel/Delmar | 1984-87 |
| Sheldon Thomas | St. Marks | 1989-92 |
| Damien Craighton | William Penn | 1993-97 |
| Bruce Kelly | St. Marks | 1995-98 |
| Andrew Donofrio | St. Marks | 1999-02 |
| Sean Dolan | St. Marks | 2007-10 |
| Codey Combs | Sussex Central | 2008-11 |
| Brent Fleetwood | Smyrna | 2011-14 |
| Gabe Giampetro | Smyrna | 2019-22 |
| Alex Poore | Caravel | 2019-22 |
| Luke Poore | Caravel | 2020-23 |
| Malachi Stratton | Sussex Central | 2022-25 |