Part of the Del Cap Festival Weekend that features other races over the two days including the Delaware Handicap, the Oaks is open to three-year-old fillies willing to race one and one-quarter miles on the dirt.
Currently, the Grade II race offers a purse of $500,000.
United States Hall of Fame fillies Gallorette (1945) and Dark Mirage (1968) have won this race as did the Canadian Horse Racing Hall of Fame inductee, Lauries Dancer.
There was no race held in 1943 and from 1983 through 1995.
| Year | Winner | Jockey | Trainer | Owner | Time |
| 2000 | Sincerely | Michael J. McCarthy | H. Graham Motion | R. Larry Johnson | 1:43.83 |
| 2001 | Zonk | Michael J. McCarthy | John Servis | Fox Hill Farms | 1:45.27 |
| 2002 | Allamerican Bertie | Larry Melancon | Steve Flint | Richard, Bertram, & Elaine Klein | 1:43.81 |
| 2003 | Island Fashion | Iggy Puglisi | Nick Canani | Everest Stable | 1:44.95 |
| 2004 | Yearly Report | Jerry D. Bailey | Bob Baffert | Golden Eagle Farm | 1:43.80 |
| 2005 | R Lady Joy | Jose Lezcano | Kirk Ziadie | Richard Averill | 1:43.25 |
| 2006 | Adieu | John R. Velazquez | Todd A. Pletcher | Tabor, Smith, Magnier | 1:43.72 |
| 2007 | Moon Catcher | Carlos Marquez, Jr. | Timothy F. Ritchey | CJZ Racing Stable/Ritchey | 1:42:39 |
| 2008 | Proud Spell | Gabriel Saez | Larry Jones | Brereton C. Jones | 1:43.34 |