| 2025 | Braden Shattuck | Rolling Green GC | 203 | Bayside Resort GC |
| 2024 | Ryan Rucinski | Wilmington CC | 204 | Fieldstone GC |
| 2023 | Michael Chanaud | The Peninsula G&CC | 201 | Bear Trap Dunes |
| 2022 | Zac Oakley | Bidermann GC | 206 | Plantation Lakes G&CC |
| 2021 | Braden Shattuck | Bidermann GC | 203 | Bidermann GC |
| 2020 | Jake Shuman | DuPont CC | 202 | The Peninsula G&CC |
| 2019 | *Brett Melton | Radley Run CC | 204 | Concord CC |
| 2018 | Braden Shattuck | Concord CC | 197 | Heritage Shores |
| 2017 | %*^Walter Egloff | Play Golf Delaware | 136 | Bear Trap Dunes |
| 2016 | ^Peter Barron, III | Play Golf Delaware | 203 | Deerfield GC |
| 2015 | Zac Oakley | DSGA Tournament Players' Club | 204 | Rehoboth Beach CC |
| 2014 | ^Christopher Hickman | Chester River Yacht & CC | 200 | Kennett Square G&CC |
| 2013 | ^Jay Whitby | Rehoboth Beach CC | 209 | Bayside Resort GC |
| 2012 | Dave McNabb | DSGA Tournament Players' Club | 204 | DuPont CC |
| 2011 | Justin Martinson | Hartefeld National GC | 202 | Kings Creek CC |
| 2010 | Eric Onesi | Hartefeld National GC | 204 | Wild Quail G&CC |
| 2009 | Justin Martinson | Hartefeld National GC | 207 | Fieldstone GC |
| 2008 | ^Amory Davis | DuPont CC | 208 | The Peninsula G&CC |
| 2007 | ^Greg Wolfe | Cavaliers CC | 218 | Hartefeld National GC |
| 2006 | ^Chris Gallagher | Penn Oaks CC | 211 | DuPont CC |
| 2005 | Dave McNabb | Cavaliers CC | 207 | Cripple Creek CC |
| 2004 | ^*Chris Anderson | Wilmington CC | 206 | Newark CC |
| Format changed to 54 holes |
| 2003 | ^Chris Anderson | Wilmington CC | 137 | Fieldstone GC |
| Format reverts to 36 holes |
| 2002 | ^Tom Borsello | Fieldstone GC | 218 | Bidermann GC |
| 2001 | ^Chris Wisler | Maple Dale CC | 204 | Deerfield G&TC |
| 2000 | Pete Oakley | Kings Creek CC | 209 | Kings Creek CC |
| 1999 | Joey Maxon | Unaffiliated | 212 | Concord CC |
| 1998 | Joey Maxon | Unaffiliated | 212 | Wilmington CC |
| Format changed to 54 holes |
| 1997 | Harold Perry | Kennett Square G&CC | 140 | Wild Quail G&CC |
| 1996 | ^Joey Maxon | Kings Creek CC | 140 | Sussex Pines CC |
| 1995 | Pete Oakley | Kings Creek CC | 143 | Radley Run CC |
| Format reverts to 36 holes |
| 1994 | ^Chris Krueger | DuPont CC | 212 | Bidermann GC |
| 1993 | Harold Perry | Kennett Square G&CC | 211 | Garrisons Lake GC |
| 1992 | Chris Anderson | Unaffiliated | 207 | Kings Creek CC & Rehoboth Beach CC |
| 1991 | ^Mike Hall | Garrisons Lake GC | 210 | DuPont CC |
| 1990 | Chris Anderson | Bidermann GC | 209 | Kennett Square G&CC |
| 1989 | Pete Oakley | Shawnee CC | 211 | Chantilly Manor CC |
| 1988 | Chris Anderson | Unaffiliated | 142 | Wilmington CC |
| 1987 | Pete Oakley | Shawnee CC | 210 | Cavaliers CC |
| 1986 | Pete Oakley | Shawnee CC | 215 | Rehoboth Beach CC |
| 1985 | Chris Anderson | Unaffiliated | 208 | Hercules CC |
| Format changed to 54 holes |
| 1984 | ^Blaise Giroso | Brandywine CC | 143 | Penn Oaks CC |
| Format reverts to 36 holes |
| 1983 | Chris Anderson | Wilmington CC | 217 | Garrisons Lake GC |
| 1982 | James Matthias | DuPont CC | 220 | Wilmington CC |
| 1981 | Larry Jones | Sussex Pines CC | 219 | Wilmington CC |
| 1980 | Pete Oakley | Rehoboth Beach CC | 202 | Hercules CC |
| 1979 | Richard Osberg | Garrisons Lake GC | 212 | Garrisons Lake GC |
| 1978 | ^Art Whaley | Rock Manor GC | 212 | Cavaliers CC |
| 1977 | Richard Osberg | Maple Dale CC | 208 | Brandywine CC |
| 1976 | Richard Osberg | Maple Dale CC | 212 | Delcastle GC |
| 1975 | Richard Osberg | Maple Dale CC | 217 | Wilmington CC |
| 1974 | Richard Osberg | Unaffiliated | 220 | Wilmington CC |
| 1973 | ^Davis Sezna | Rehoboth Beach CC | 221 | Garrisons Lake GC |
| 1972 | William Hackett | Delcastle GC | 216 | Rock Manor GC, Delcastle GC & Concord CC |
| 1971 | ^Ted Till | DuPont CC | 218 | Radley Run CC, Penn Oaks CC, Newark CC |
| Format changes to 54 holes |
| 1970 | ^Richard Osberg | Hercules CC | 141 | Hercules CC |
| 1969 | *Robert Holzman, Jr. | Wilmington CC | 146 | Brandywine CC & Radley Run CC |
| 1968 | John Long | DuPont CC | 147 | Wilmington CC |
| 1967 | ^Louis Nieliwocki | DuPont CC | 147 | DuPont CC |
| 1966 | Clint Kennedy | Rock Manor GC | 145 | Rehoboth Beach CC |
| ^Amateur |
| %Shortened to 36 holes due to weather |
| *Won in a playoff |