Team Champions - Division 2 (1993-2026)
| Year | Champion | Coach | Runner-Up | Coach | Score |
|---|---|---|---|---|---|
| 1993 | Smyrna | Mike Dulin | Middletown | Ed Manlove | 45-7 |
| 1994 | Smyrna | Mike Dulin | Hodgson Vo. Tech | Jerry Lamey | 47-10 |
| 1995 | AI Dupont | George Lacsny | Smyrna | Mike Dulin | 36-19 |
| 1996 | Smyrna | Mike Dulin | Hodgson | Jerry Lamey | 35-28 |
| 1997 | Hodgson | Jerry Lamey | Smyrna | Mike Dulin | 41-20 |
| 1998 | Hodgson | Jerry Lamey | Smyrna | Mike Dulin | 53-15 |
| 1999 | Hodgson | Jerry Lamey | Milford | Don Parsley | 44-11 |
| 2000 | Hodgson | Jerry Lamey | Milford | Don Parsley | 44-16 |
| 2001 | Hodgson | Jerry Lamey | Lake Forest | Scott Fleming | 45-18 |
| 2002 | Hodgson | Jerry Lamey | Smyrna | Clay Lloyd | 42-18 |
| 2003 | Smyrna | Clay Lloyd | Laurel | Tom Povia | 37-31 |
| 2004 | Milford | Don Parsley | Smyrna | David Morrison | 42-25 |
| 2005 | Smyrna | Kurt Howell | Hodgson | Stan Spoor | 52-6 |
| 2006 | Hodgson | Stan Spoor | Caravel | Matt Zambanini | 36-32 |
| 2007 | Hodgson | Stan Spoor | Smyrna | Kurt Howell | 38-24 |
| 2008 | Hodgson | L.A. Collier | Indian River | Jeff Windish | 37-30 |
| 2009 | Milford | Don Parsley | Hodgson | L.A. Collier | 37-33 |
| 2010 | Hodgson | Dave Williams | Caravel | Mike Welch | 35-34 |
| 2011 | Caravel | Mike Welch | Indian River | Jeff Windish | 44-34 |
| 2012 | Polytech | Dan Boone | St. Georges Tech | Nate Pellegrini | 36-26 |
| 2013 | St. Georges Tech | Nate Pellegrini | Polytech | Eric Buckson | 35-22 |
| 2014 | Milford | Dan Rigby | St. Georges Tech | Nate Pellegrini | 42-20 |
| 2015 | Milford | Dan Rigby | Sanford | Corey Frederick | 36-24 |
| 2016 | Milford | Don Parsley | St. Georges Tech | Patrick Atkinson | 57-24 |
| 2017 | Milford | Don Parsley | Indian River | Jeff Windish | 32-30 |
| 2018 | Milford | Don Parsley | Laurel | Jesse Glanden | 38-29 |
| 2019 | Milford | Don Parsley | Caravel | Mike Welch | 37-30 |
| 2020 | Caravel | Mike Welch | Woodbridge | Shane Marvel | 57-7 |
| 2021 - No Tournament (COVID) | |||||
| 2022 | Caravel | Mike Welch | Delaware Military Academy | L.A. Collier | 52-15 |
| 2023 | Delaware Military Academy | L.A. Collier | Caravel | Mike Welch | 36-24 |
| 2024 | Delaware Military Academy | L.A. Collier | St. Marks | Cameron Butler | 38-32 |
| 2025 | Delaware Military Academy | L.A. Collier | St. Marks | Cameron Butler | 42-24 |
| 2026 | Delaware Military Academy | L.A. Collier | Laurel | Zach Toadvine | 52-17 |
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