| Year |
Delaware District 1 |
Delaware State |
Eastern Regional |
LLWS |
| 2025 | Camden-Wyoming | Millsboro | Oxford (MA) | Guaynabo, Puerto Rico |
| 2024 | Camden-Wyoming | Camden-Wyoming | Auburn (MA) | Coquivacoa, Venezuela |
| 2023 | Camden-Wyoming | Millsboro | Cherry Hill (NJ) | Willemstad, Curaçao |
| 2022 | Dover | Georgetown | Vineland (NJ) | Guayama, Puerto Rico |
| 2021 | Camden-Wyoming | Brandywine | - | - |
| 2020 | - | - | - | - |
| 2019 | Smyrna-Clayton | Naamans | Naamans (DE) | Wailuku, Hawaii |
| 2018 | Dover | Naamans | Naamans (DE) | Willemstad, Curaçao |
| 2017 | Dover | Naamans | West Deptford Township (NJ) | Aguadulce, Panama |
| 2016 | Smyrna-Clayton | Millsboro | Clifton (NJ) | Chicago, Illinois |
| 2015 | Smyrna-Clayton | Cape Henlopen | Upper Moreland (PA) | Houston, East Texas |
| 2014 | Milford | Cape Henlopen | Bristol (CT) | Houston, East Texas |
| 2013 | Milford | Naamans | Kennett Square (PA) | Chitré, Panama |
| 2012 | Camden-Wyoming | Naamans | Auburn (MA) | Guatemala City, Guatemala |
| 2011 | Harrington | Harrington | Talbot County (MD) | Hilo, Hawaii |
| 2010 | Smyrna-Clayton | Naamans | Vineland (NJ) | San Nicolaas, Aruba |
| 2009 | Dover | Naamans | Vineland (NJ) | Houston, East Texas |
| 2008 | Camden-Wyoming | Naamans | Upper Deerfield (NJ) | Upper Deerfield Township, New Jersey |
| 2007 | MOT | MOT | Freehold Township (NJ) | Cartersville, Georgia |
| 2006 | Camden-Wyoming | Camden-Wyoming | Bloomfield (NJ) | Punto Fijo, Venezuela |
| 2005 | Camden-Wyoming | Camden-Wyoming | Freehold Township (NJ) | Urbandale, Iowa |
| 2004 | Dover | Dover | Freehold Township (NJ) | Freehold Township, New Jersey |
| 2003 | Milford | Milford | Vineland (NJ) | Hilo, Hawaii |