| 2023 | Blake Micholas | Kings Creek CC | | | 270 | Wild Quail G&CC |
| 2022 | Jacoby Chappa | Maple Dale CC | | | 292 | Bayside Resort GC |
| 2021 | Michael R. Brown, Jr. | Play Golf Delaware | | | 273 | Newark CC |
| 2020 | *Dawson Anders | Play Golf Delaware | | | 274 | Heritage Shores GC |
| 2019 | Evan Brown | DuPont CC | | | 283 | Maple Dale CC |
| 2018 | Peter Barron, III | Play Golf Delaware | | | 276 | Odessa National GC |
| 2017 | Jay Whitby | Rehoboth Beach CC | | | 278 | The Rookery North |
| 2016 | Jay Whitby | Rehoboth Beach CC | | | 279 | Wild Quail G&CC |
| 2015 | Jay Whitby | Rehoboth Beach CC | | | 280 | Heritage Shores GC |
| 2014 | Christopher Hickman | Chester River Y&TC | | | 281 | Cavaliers CC |
| 2013 | Christopher Hickman | Chester River Y&TC | | | 268 | Odessa National GC |
| 2012 | PJ Tighe | Frog Hollow GC | | | 282 | Frog Hollow GC |
| 2011 | *Dan Ott | Frog Hollow GC | | | 283 | Back Creek GC |
| 2010 | Justin Martinson | Hartefeld National | | | 281 | Wilmington CC |
| 2009 | Greg Wolfe | Cavaliers CC | | | 287 | Cripple Creek CC |
| 2008 | Eric Onesi | Fieldstone GC | | | 279 | Cavaliers CC |
| 2007 | *Amory Davis | Bidermann GC | | | 296 | Bayside Resort GC |
| 2006 | Jay Whitby | Wild Quail G&CC | | | 287 | Wild Quail G&CC |
| 2005 | Chris Anderson | Wilmington CC | | | 290 | Wilmington CC |
| 2004 | Jeff Osberg | The Club at Patriots Glen | | | 282 | Back Creek GC |
| 2003 | Rich Pruchnik | West Chester G&CC | | | 293 | Kings Creek CC |
| 2002 | Otto J. Juhl | Deerfield G&TC | | | 287 | Three Little Bakers CC |
| 2001 | Chris Wisler | Maple Dale CC | | | 275 | Sussex Pines CC |
| 2000 | Chris Wisler | Maple Dale CC | | | 280 | DuPont CC |
| 1999 | Chris Wisler | Maple Dale CC | | | 284 | Deerfield G&TC |
| 1998 | Joey Maxon | Maple Dale CC | | | 274 | Cripple Creek CC |
| 1997 | Joey Maxon | Maple Dale CC | | | 282 | Maple Dale CC |
| 1996 | Otto J. Juhl | Cavaliers CC | | | 291 | Cavaliers CC |
| 1995 | Chris Krueger | DuPont CC | | | 286 | Three Little Bakers CC & Hercules CC |
| 1994 | Blaise Giroso | Brandywine CC | | | 285 | Wilmington CC |
| 1993 | Blaise Giroso | Brandywine CC | | | 281 | Wild Quail G&CC |
| 1992 | Tom Borsello | Chantilly Manor CC | | | 285 | Chantilly Manor CC |
| 1991 | Blaise Giroso | Brandywine CC | | | 272 | Brandywine CC |
| 1990 | Blaise Giroso | Brandywine CC | | | 282 | Newark CC |
| 1989 | Blaise Giroso | Brandywine CC | | | 285 | Hercules CC |
| 1988 | Mike Hall | Garrisons Lake | | | 290 | Concord CC |
| 1987 | Blaise Giroso | Brandywine CC | | | 292 | Garrisons Lake GC |
| 1986 | Blaise Giroso | Brandywine CC | | | 294 | DuPont CC |
| 1985 | Mike Hall | Garrisons Lake GC | | | 287 | Garrisons Lake GC |
| 1984 | Blaise Giroso | Brandywine CC | | | 281 | DuPont CC |
| 1983 | John Corzilius | Cavaliers CC | | | 291 | Maple Dale CC |
| 1982 | John Corzilius | Cavaliers CC | | | 280 | DuPont CC |
| 1981 | Mike Hall | Garrisons Lake GC | | | 281 | Pike Creek Valley GC |
| 1980 | Blaise Giroso | Cavaliers CC | | | 290 | Cavaliers CC |
| 1979 | Blaise Giroso | Rock Manor GC | | | 294 | Pike Creek Valley GC |
| 1978 | Jeffrey Osberg | Garrisons Lake GC | | | 283 | Hercules CC |
| 1977 | Shaun Prendergast | DuPont CC | | | 287 | DuPont CC |
| 1976 | James Powell | Pike Creek Valley GC | | | 298 | Pike Creek Valley GC |
| 1975 | David Corzilius | Wilmington CC | | | 288 | Garrisons Lake GC |
| 1974 | Shaun Prendergast | DuPont CC | | | 297 | Garrisons Lake GC |
| Format changes to Stroke Play (72 holes) |
| 1973 | David Corzilius | Rock Manor GC | Robert Murphy | Rock Manor GC | 3&1 | Delcastle GC, DuPont CC, Newark CC |
| 1972 | Richard Osberg | Hercules CC | William Harman, Jr. | Wilmington CC | 8&6 | Cavaliers CC & Wilmington CC |
| Format changes to Match Play |
| 1971 | Ed Richitelli | Wilmington CC | | | 299 | Radley Run CC & Garrisons Lake GC |
| 1970 | Ed Richitelli | Wilmington CC | | | 301 | Wilmington CC & Rehoboth Beach CC |
| 1969 | *James Monkman | Wilmington CC | | | 292 | DuPont CC (Louviers) & Newark CC |
| 1968 | *Robert Murphy | Rock Manor GC | | | 291 | Rock Manor GC & Greenhill GC |
| 1967 | Louis Nieliwocki | DuPont CC | | | 296 | Brandywine CC & Cavaliers CC |
| 1966 | Roy Marquette | DuPont CC | | | 294 | Wilmington CC & Hercules GC |
| 1965 | Daryl Nieliwocki | DuPont CC | | | 293 | Newark CC |
| Format changes to Stroke Play (72 holes) |
| 1964 | Robert DeFiore | Cavaliers CC | William Ferguson | DuPont CC | 3&1 | Brandywine CC |
| 1963 | Ellis Taylor | Cavaliers CC | Lou Nieliwocki | DuPont CC | 5&4 | Rock Manor GC |
| 1962 | Roy Marquette | DuPont CC | Rudy Otteni | DuPont CC | 7&5 | DuPont CC |
| 1961 | Louis Nieliwocki | DuPont CC | Bill Ferguson | DuPont CC | 3&1 | Concord CC |
| 1960 | Ellis Taylor | Rock Manor GC | Paul DiElenterio | Cavaliers CC | 5&3 | Seaford CC |
| 1959 | Jack Vaile | Hercules CC | Ellis Taylor | Rock Manor GC | 3&1 | Hercules CC |
| 1958 | Ellis Taylor | Rock Manor GC | Willard Dickerson | Rock Manor GC | 3&2 | Newark CC |
| 1957 | Ellis Taylor | Rock Manor GC | Earle Blood | Rock Manor GC | 3&2 | Rock Manor GC |
| 1956 | John Gehret | Concord CC | Ray Marquette | DuPont CC | 3&2 | Brandywine CC |
| 1955 | Roy Marquette | DuPont CC | Paul DiElenterio | Rock Manor GC | 1-up | DuPont CC |
| 1954 | George Anderson | Concord CC | Vic Catalino | Rock Manor GC | 5&3 | Concord CC |
| 1953 | Ellis Taylor | Rock Manor GC | George Anderson | Newark CC | 4&3 | Hercules CC |
| 1952 | Albert Dollins | Newark CC | Ronnie Wollaston | Newark CC | 2&1 | DuPont CC |
| *Won in a playoff | | | | | | |
