| Year | Champion | Club | Score | Venue |
| 2025 | Oscar Mestre | Overbrook GC | 135 | The Rookery GC |
| 2024 | Tom Humphrey | Wilmington CC | 147 | Plantation Lakes G&CC |
| 2023 | Steve Walczak | Wilmington CC | 136 | Frog Hollow GC |
| 2022 | Alan Wagenschnur | Newark CC | 142 | Newark CC |
| 2021 | Mike Owsik | Play Golf Delaware | 138 | Rock Manor GC |
| 2020 | Paul Dillon | Cripple Creek CC | 151 | White Clay Creek CC |
| 2019 | #Gary Dornhoefer | Wild Quail G&CC | 107 | Rehoboth Beach CC |
| 2018 | Pete Widdoes | White Clay Creek CC | 144 | Wild Quail G&CC |
| 2017 | Ray Pawulich | Play Golf Delaware | 157 | Newark CC |
| 2016 | *Ray Pawulich | Play Golf Delaware | 152 | Maple Dale CC |
| *Won in a playoff | | | | |
