| Year |
Delaware District 1 |
Delaware State |
Eastern Regional |
LLWS |
| 2025 | Milford | Milford | Indiana (PA) | Columbus, Texas |
| 2024 | Felton-Harrington | Western Sussex | Indiana (PA) | Prague, Czech Republic |
| 2023 | Camden-Wyoming | Lower Sussex | Milford (CT) | Bago City, Philippines |
| 2022 | MOT | MOT | Milford (CT) | Jenison, Michigan |
| 2021 | Camden-Wyoming | Lower Sussex | - | - |
| 2020 | - | - | - | - |
| 2019 | Dover | Laurel-Millsboro-Nanticoke | Haverstraw (NY) | Tampa, Florida |
| 2018 | Camden-Wyoming | Laurel-Millsboro-Nanticoke | Cranston National (RI) | Santa Clara, Utah |
| 2017 | Milford | Laurel-Nanticoke | Warwick North (RI) | Poland, Ohio |
| 2016 | Camden-Wyoming | Camden-Wyoming | Warwick North (RI) | Maunabo, Puerto Rico |
| 2015 | Camden-Wyoming | Lower Sussex | Pawcutuck-Mystic-Westerly (RI/CT) | Tampa, Florida |
| 2014 | Camden-Wyoming | Georgetown-Millsboro | West Point (PA)
| West Point, Pennsylvania |
| 2013 | Camden-Wyoming | Georgetown-Millsboro | West Cumberland (PA) | Tampa, Florida |
| 2012 | Camden-Wyoming | Georgetown-Millsboro | West Haven (CT) | Anchorage, Alaska |
| 2011 | Milford | Milford | West Point (PA) | Crosswell, Michigan |
| 2010 | Milford | Canal | West Point (PA) | Maunabo, Puerto Rico |
| 2009 | MOT | Woodbridge | Nanticoke-Newport Township (PA) | Maunabo, Puerto Rico |
| 2008 | Felton-Harrington | Felton-Harrington | West Point (PA) | Ora Valley, Arizona |
| 2007 | Milford | Milford | Haverstraw (NY) | Maunabo, Puerto Rico |
| 2006 | Milford | Laurel | West Point (PA) | Naples, Florida |
| 2005 | Milford | Canal | Milton (PA) | Lake Wales, Florida |
| 2004 | Milford | Seaford | Milton (PA) | South Bend, Indiana |
| 2003 | Camden-Wyoming | Laurel | Nippenose Valley (NJ) | Bacolod, Philippines |