Team Champions - Division 1 (1993-2026)
| Year | Champion | Coach | Runner-Up | Coach | Score |
|---|---|---|---|---|---|
| 1993 | William Penn | Jack Holloway | Dover | Harry Rigby | 40-17 |
| 1994 | William Penn | Jack Holloway | Dover | Harry Rigby | 39-9 |
| 1995 | St. Mark's | Steve Bastianelli | Sussex Central | Phil Shultie | 46-19 |
| 1996 | William Penn | Jack Holloway | St. Mark's | Steve Bastianelli | 33-20 |
| 1997 | St. Mark's | Steve Bastianelli | Caesar Rodney | Dicky Howell | 43-12 |
| 1998 | St. Mark's | Steve Bastianelli | Caesar Rodney | Dicky Howell | 48-15 |
| 1999 | St. Mark's | Steve Bastianelli | Sussex Central | Phil Shultie | 30-21 |
| 2000 | William Penn | Jack Holloway | St. Mark's | Steve Bastianelli | 25-23 |
| 2001 | Caesar Rodney | Dicky Howell | St. Mark's | Steve Bastianelli | 31-27 |
| 2002 | St. Mark's | Steve Bastianelli | Caesar Rodney | Dicky Howell | 36-24 |
| 2003 | Caesar Rodney | Dicky Howell | St. Mark's | Steve Bastianelli | 25-23 |
| 2004 | Caesar Rodney | Dicky Howell | St. Mark's | Jason Bastianelli | 41-16 |
| 2005 | Caesar Rodney | Dicky Howell | St. Mark's | Jason Bastianelli | 52-10 |
| 2006 | Caesar Rodney | Dicky Howell | St. Mark's | Jason Bastianelli | 38-15 |
| 2007 | Caesar Rodney | Dicky Howell | St. Mark's | Jason Bastianelli | 44-12 |
| 2008 | Sussex Central | Phil Shultie | Caesar Rodney | Dicky Howell | 33-24 |
| 2009 | St. Mark's | Jason Bastianelli | Caesar Rodney | Dicky Howell | 44-15 |
| 2010 | St. Mark's | Jason Bastianelli | Sussex Central | Phil Shultie | 39-23 |
| 2011 | Caesar Rodney | Dicky Howell | St. Mark's | L.A. Collier | 36-24 |
| 2012 | Caesar Rodney | Dicky Howell | Smyrna | Kurt Howell | 32-24 |
| 2013 | Smyrna | Kurt Howell | Caesar Rodney | Dicky Howell | 36-24 |
| 2014 | Smyrna | Kurt Howell | Caesar Rodney | Dicky Howell | 43-17 |
| 2015 | Smyrna | Kurt Howell | Polytech | Eric Buckson | 34-22 |
| 2016 | Smyrna | Kurt Howell | Sussex Central | Phil Shultie | 50-15 |
| 2017 | Sussex Central | Phil Shultie | Smyrna | Kurt Howell | 32-30 |
| 2018 | Caesar Rodney | Dan Rigby | Smyrna | Kurt Howell | 30-29 |
| 2019 | Smyrna | Aaron Harris | Caesar Rodney | Dan Rigby | 35-33 |
| 2020 | Smyrna | Aaron Harris | Milford | Don Parsley | 36-34 |
| 2021 - No Tournament (COVID) | |||||
| 2022 | Cape Henlopen | Chris Mattioni | Caesar Rodney | Dan Rigby | 43-26 |
| 2023 | Salesianum | Cameron Davis | Cape Henlopen | Chris Mattioni | 36-27 |
| 2024 | Sussex Central | Shane Miller | Cape Henlopen | Chris Mattioni | 36-34 |
| 2025 | Salesianum | Cameron Davis | Sussex Central | Shane Miller | 43-28 |
| 2026 | Salesianum | Cameron Davis | Caesar Rodney | Trey Mitchell | 59-9 |
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