| 2025 | Joe Roeder | Merion GC | 136 | Rock Manor GC | | |
| 2024 | Neil Gordon | Doylestown CC | 143 | Bear Trap Dunes (Black Bear/Grizzly) | | |
| 2023 | Ron Jamarowicz | DuPont CC | 141 | DuPont CC (Nemours/DuPont) | | |
| 2022 | Rufino Rosal | DuPont CC | 137 | Wild Quail G&CC | | |
| 2021 | Ron Jamarowicz | DuPont CC | 142 | Heritage Shores | | |
| 2020 | Tom Borsello | DuPont CC | 144 | Hartefeld National GC | | |
| 2019 | John Gosselin | Kennett Square G&CC | 142 | Back Creek GC | | |
| 2018 | Tom Humphrey | Wilmington CC | 141 | Deerfield GC | | |
| 2017 | Chris Smedley | N/A | 144 | Odessa National GC | | |
| 2016 | Jeffrey Allen | N/A | 142 | The Rookery North GC | | |
| 2015 | Steve Walczak | N/A | 142 | Wild Quail G&CC | | |
| 2014 | John Register | N/A | 113 | Wilmington CC | | |
| 2013 | Tom Borsello | N/A | 147 | Kings Creek CC | | |
| 2012 | Mark Surtees | N/A | 142 | Newark CC | | |
| 2011 | Mark Surtees | N/A | 145 | Odessa National GC | | |
| 2010 | Mark Surtees | Back Creek GC | 142 | Back Creek GC | | |
| 2009 | Stan Zabytko | Kings Creek CC | 150 | The Peninsula G&CC | | |
| 2008 | Charles McClaskey | The Club at Patriots Glen | 142 | Newark CC | | |
| 2007 | *Charles McClaskey | The Club at Patriots Glen | 147 | Brandywine CC | | |
| 2006 | *Charles McClaskey | The Club at Patriots Glen | 145 | Rehoboth Beach CC | | |
| 2005 | Jim DeBrusk | The Club at Patriots Glen | 144 | Shawnee CC | | |
| 2004 | Charles McClaskey | The Club at Patriots Glen | 142 | Delaware National CC | | |
| 2003 | David Smithburger | Three Little Bakers CC | 151 | Christiana CC | | |
| 2002 | George Clenney | Caroline CC | 148 | Wild Quail G&CC | | |
| 2001 | Charles McDowell | Wilmington CC | 148 | Baywood Greens GC | | |
| 2000 | George Clenney | Caroline CC | 147 | Maple Dale CC | | |
| 1999 | Charles McClaskey | Chantilly Manor GC | 145 | Newark CC | | |
| 1998 | #*Yogish Patel | Wilmington CC | 72 | Brantwood GC | | |
| 1997 | Bill Wolhar | Wilmington CC | 141 | Cavaliers CC | | |
| 1996 | Sandy Knapp | DuPont CC | 150 | Cripple Creek G&CC | | |
| 1995 | *Adam Freccia | Rock Manor GC | 150 | Wild Quail G&CC | | |
| 1994 | Lew Blakey | Rehoboth Beach | 144 | Shawnee CC | | |
| 1993 | Frank Kaminski | Porky Oliver GC | 145 | DuPont CC | | |
| 1992 | Don Thompson | Kennett Square G&CC | 143 | Rock Manor GC | | |
| 1991 | William Campbell | Wilmington CC | 149 | Hercules CC | | |
| 1990 | Bob Kauffield | DuPont CC | 147 | Brandywine CC | | |
| 1989 | Joe Sylvester | DuPont CC | 148 | Cavaliers CC | | |
| 1988 | Jim Hohman | DuPont CC | 141 | DuPont CC | | |
| Format changed to 36-hole individual stroke play |
| 1987 | Jim Hohman | DuPont CC | 230 | Maple Dale CC | | |
| 1986 | ^Jim Hohman | DuPont CC | 150 | Newark CC | | |
| 1985 | Adam Freccia | Rock Manor GC | 229 | Cavaliers CC | | |
| Format changed to 54-hole individual stroke play |
| 1984 | Ed Richitelli | Brantwood GC | 149 | Chantilly Manor CC | | |
| 1983 | Elwood Statler | Newark CC | 148 | Newark CC | | |
| 1982 | Jack Rivers | Wilmington CC | 153 | Brandywine CC | | |
| 1981 | Jack Rivers | Wilmington CC | 146 | Delcastle GC | | |
| 1980 | Louis Nieliwocki | DuPont CC | 145 | Greenhill CC | | |
| 1979 | Joe Sylvester | Rock Manor GC | 145 | Rock Manor GC | | |
| 1978 | Ed Richitelli | Newark CC | 149 | Newark CC | | |
| 1977 | Ed Richitelli | Wilmington CC | 151 | Cavaliers CC | | |
| 1976 | Joe Sylvester | Rock Manor GC | 141 | Brantwood GC | | |
| 1975 | Joe Sylvester | Rock Manor GC | 148 | Newark CC | | |
| 1974 | Steve Brodie | DuPont CC | 145 | Hercules CC | | |
| 1973 | Louis Nieliwocki | DuPont CC | 148 | Brandywine CC | | |
| 1972 | *Ed Richitelli | Wilmington CC | 152 | Rehoboth Beach CC | | |
| 1971 | *Steve Brodie | DuPont CC | 153 | Brandywine CC | | |
| 1970 | Wally Sezna | Radley Run CC | 148 | Newark CC | | |
| 1969 | Steve Brodie | DuPont CC | 152 | Rock Manor GC | | |
| 1968 | Vincent DeCampie | Rock Manor GC | 147 | Greenhill CC | | |
| 1967 | Willard B. McConnell | Greenhill GC | 145 | Kennett Square G&CC | | |
| 1966 | *Willard B. McConnell | Greenhill GC | 152 | Garrisons Lake GC | | |
| 1965 | *Willard B. McConnell | Greenhill GC | 153 | Cavaliers CC | | |
| 1964 | Willard B. McConnell | Greenhill GC | 150 | Maple Dale CC | | |
| 1963 | Victor Lichtenstein | Rehoboth Beach CC | 152 | Rehoboth Beach CC | | |
| 1962 | Willard B. McConnell | Greenhill CC | 144 | Rehoboth Beach CC | | |
| 1961 | Willard Dickerson | Cavaliers CC | 151 | Rehoboth Beach CC | | |
| 1960 | Howard A. Turner, Jr. | Wilmington CC | 156 | Newark CC | | |
| 1959 | Willard Dickerson | Cavaliers CC | 146 | DuPont CC | | |
| 1958 | Dallas Culver | Rehoboth Beach CC | 160 | Rehoboth Beach CC | | |
| 1957 | Arthur Dezendorf | Rehoboth Beach CC | 146 | Rehoboth Beach CC | | |
| 1956 | James Bobb | Rock Manor GC | 170 | Rehoboth Beach CC | | |
| 1955 | Charles L. Baldo | DuPont CC | 164 | Rehoboth Beach CC | | |
| Format changed to 36-hole individual stroke play |
| 1954 | *Frank L. Uhl, Jr. | Newark CC | 80 | Brandywine CC | | |
| 1953 | Ralph Dawson | Rehoboth Beach CC | 78 | Maple Dale CC | | |
| 1952 | Charles L. Baldo | DuPont CC | 76 | Newark CC | | |
| *Won in playoff | | | | | | |
| ^36-hole event due to weather | | | | | | |
| #18-hole event due to weather | | | | | | |