Maryland Million Oaks
$100,000, 3-year-old fillies, 1 mile
| Year | Winner | Owner | Breeder | Trainer | Jockey | Time |
| 1986 | Smart n Quick | J. B. Merryman | same | Katherine M. Voss | A. Delgado | 01:51.00 |
| 1987 | Angelina County | Carey K. Miller | same | J. William Boniface | M. G. Pino | 01:50.00 |
| 1988 | Oh My Pride | Ivy Dell Stud | same | Michael J. Moran | J. A. Santos | 01:51.00 |
| 1989 | Beware of the Cat | Ryehill Farm | same | Lazaro S. Barrera | E. Maple | 01:50.00 |
| 1990 | McKilts | DanDar Farm | North Highland Farm | W. Meredith Bailes | J. Rocco | 01:50.00 |
| 1991 | Richards Lass | Robert M. Perez | Allen E. Paulson | Alfredo Callejas | J. F. Chavez | 01:42.00 |
| 1992 | Deputation | Stuart S. Janney III | same | Claude R. McGaughey III | J. A. Krone | 01:44.00 |
| 1993 | Champion Jay | Herman J. Kossow | same | Carlos A. Garcia | E. S. Prado | 01:50.00 |
| 1994 | Churchbell Chimes | Susan Granville | Bonita Farm | J. William Boniface | A. Delgado | 01:50.00 |
| 1995 | Urbane | Jan, Mace and Samantha Siegel | Violet Cleveland and Frank Zureick | Randy Bradshaw | C. S. Nakatani | 01:50.00 |
| 1996 | The Rulers Sister | Chiles & Childs Stable | Rebecca Bowman Davis | Donald H. Barr | E. S. Prado | 01:49.00 |
| 1997 | Proud Run | Katharine W. Merryman | same | Richard J. Hendriks | N. Santagata | 01:51.00 |
| 1998 | Maragold Princess | Michael Cascio | Ryver Meadow Farms | Todd A. Pletcher | E. S. Prado | 01:51.00 |
| 1999 | Saratoga Friends | Saratoga Friends Stable | Glade Valley Farms Inc. | Anthony W. Dutrow | R. Wilson | 01:51.00 |
| 2000 | Gin Talking | Skeedattle Associates | Barbara C. Graham | Robin L. Graham | R. A. Dominguez | 01:48.71 |
| 2001 | Along Came Mary | Gerald A. Nielsen | Mr. and Mrs. Gerald Nielsen | H. James Bond | T. L. Dunkelberger | 01:45.71 |
| 2002 | Undercover | Anthony W. Dutrow | Dr. and Mrs. Thomas Bowman and Allen’s Prospect Synd. | Anthony W. Dutrow | M. G. Pino | 01:43.90 |
| 2003 | River Cruise | Sondra D. Bender | Sondra Bender and Howard M. Bender | Lawrence E. Murray | Jeremy Rose | 01:50.65 |
| 2004 | Silmaril | Stephen E. Quick and Christopher J. Feifarek | same | Christopher W. Grove | Abel Castellano Jr. | 01:43.98 |
| 2005 | Sticky | Fitzhugh LLC | Robert E. Meyerhoff | Richard W. Small | J. Z. Santana | 01:54.20 |
| 2006 | Smart and Fancy | Win and Place Stable | Dr. and Mrs. Thomas Bowman | Anthony W. Dutrow | Jeremy Rose | 01:37.34 |
| 2007 | Moon Catcher | CJZ Racing Stable & Timothy F. Ritchie | Albert H., Randy L. Cohen & A. Ferris Allen III | Timothy F. Ritchie | Tony Black | 01:37.47 |
| 2008 | Sweet Goodbye | William R. Harris | same | Christopher W. Grove | J. D. Acosta | 01:38.47 |
| 2009 | Love That Dance | John Petrini | same | Ben Perkins Jr. | Carlos Marquez Jr. | 01:36.40 |
| 2010 | Baltimore Belle | Robert Gerczak and Kaygar Stable | Carol Kaye-Garcia and Barbara Smith | John B. Secor | V. Diaz | 01:38.35 |
| 2011 | Brushed By Love | Nona Lisa Stables LLC | Bowman & Higgins Stable, T. Sutton & Huckleberry Farm LLC | Michael Trobetta | Julian Pimentel | 01:38.68 |
| 2012 | Jazzy Idea | Edwin W. Merryman | Mr. & Mrs. Edwin W. Merryman | Edwin Merryman | E. Trujillo | 01:38.64 |
- Run at 1 1/16 miles 1991, 1992, 2001, 2002 and 2004
- Run as Omni International Maryland Oaks 1986, 1987
- Kennard Warfield Jr. Group Maryland Oaks 1988 through 1990
- Challedon Society Maryland Oaks 1993
- Diamond Comics Superheroine Maryland Oaks 1994
- Baltimore Magazine Maryland Oaks 1995 through 1998
- Baltimore Sun Maryland Oaks 1999 through 2002
- Cosequin® Maryland Oaks 2004
- Maryland Lottery Oaks 2007
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