Winners of The Diana Handicap Since 1939
| Year |
Winner |
Age |
Jockey |
Trainer |
Owner |
Distance (Miles) |
Time |
Grade |
| 2012 | Winter Memories | 4 | Javier Castellano | James J. Toner | Phillips Racing | 1-1/8 | 1:48.50 | I |
| 2011 | Zagora | 4 | Javier Castellano | Chad Brown | Martin S. Schwartz | 1-1/8 | 1:49.19 | I |
| 2010 | Proviso | 5 | Mike E. Smith | William I. Mott | Juddmonte Farms | 1-1/8 | 1:47.04 | I |
| 2009 | Forever Together | 5 | Julien Leparoux | Jonathan Sheppard | Augustin Stable | 1-1/8 | 1:48.21 | I |
| 2008 | Forever Together | 4 | Julien Leparoux | Jonathan Sheppard | Augustin Stable | 1-1/8 | 1:46.52 | I |
| 2007 | My Typhoon | 5 | Eddie Castro | William I. Mott | Live Oak Plantation | 1-1/8 | 1:46:47 | I |
| 2006 | Angara | 5 | Fernando Jara | William I. Mott | Sangster Family Stable | 1-1/8 | 1:49.20 | I |
| 2005 | Sand Springs | 5 | John Velazquez | William I. Mott | Sangster Family Stable | 1-1/8 | 1:46.91 | I |
| 2004 | Wonder Again | 5 | Edgar Prado | James J. Toner | Phillips Racing Partners | 1-1/8 | 1:48.99 | I |
| 2003 | Voodoo Dancer | 5 | Corey Nakatani | Christophe Clement | Green Hills Farm | 1-1/8 | 1:47.98 | I |
| 2002 | Tates Creek | 4 | Jerry Bailey | Robert J. Frankel | Juddmonte Farms | 1-1/8 | 1:48.00 | II |
| 2001 | Starine | 4 | John Velazquez | Robert J. Frankel | Robert J. Frankel | 1-1/8 | 1:46.17 | II |
| 2000 | Perfect Sting | 4 | Jerry Bailey | Joseph Orseno | Stronach Stable | 1-1/8 | 1:47.01 | II |
| 1999 | Heritage Of Gold | 4 | Shane Sellers | Thomas Amoss | Jack Garey | 1-1/8 | 1:45.93 | II |
| 1998 | Memories of Silver | 5 | Jerry Bailey | James J. Toner | Joan Phillips | 1-1/8 | 1:46.14 | II |
| 1997 | Rumpipumpy | 4 | Jose Santos | Christophe Clement | Gaye MacRae | 1-1/8 | 1:48.59 | II |
| 1996 | Electric Society | 5 | Mike E. Smith | John C. Kimmel | Gary A. Tanaka | 1-1/8 | 1:46.56 | II |
| 1995 | Perfect Arc | 3 | John Velazquez | Angel Penna, Jr. | Brazil Stables | 1-1/8 | 1:46.85 | II |
| 1994 | Via Borghese | 5 | Jose Santos | Angel Penna, Jr. | Malcolm E. Parrish | 1-1/8 | 1:52.01 | II |
| 1993 | Ratings | 5 | Julie Krone | Jonathan Sheppard | Augustin Stable | 1-1/8 | 1:49.80 | II |
| 1992 | Plenty of Grace | 5 | Herb McCauley | John M. Veitch | Darby Dan Farm | 1-1/8 | 1:46.66 | II |
| 1991 | Christiecat | 4 | Jean-Luc Samyn | Patrick J. Kelly | Fox Ridge Farm | 1-1/8 | 1:47.66 | II |
| 1990 | Foresta | 4 | Angel Cordero, Jr. | Thomas Bohannan | Loblolly Stable | 1-1/8 | 1:48.40 | II |
| 1989 | Glowing Honor | 4 | Jerry Bailey | MacKenzie Miller | Rokeby Stable | 1-1/8 | 1:50.20 | II |
| 1988 | Glowing Honor | 3 | Pat Day | MacKenzie Miller | Rokeby Stable | 1-1/8 | 1:49.40 | II |
| 1987 | Bailrullah | 5 | Jean Cruguet | William W. Wright | Laura Leigh Stable | 1-1/8 | 1:46.20 | II |
| 1986 | Duty Dance | 4 | Jean Cruguet | C. R. McGaughey III | Ogden Mills Phipps | 1-1/8 | 1:49.80 | II |
| 1985 | Lake Country | 4 | Jeffrey Fell | Jack Ludwig | Stephen Dennehy | 1-1/8 | 1:48.40 | II |
| 1984 | Wild Applause | 3 | Walter Guerra | MacKenzie Miller | Rokeby Stable | 1-1/8 | 1:48.20 | II |
| 1983 | Hush Dear | 5 | Jacinto Vasquez | J. Elliott Burch | C. V. Whitney | 1-1/8 | 1:48.40 | II |
| 1983 | Geraldine's Store | 4 | Jean-Luc Samyn | Philip G. Johnson | Thomas P. Whitney | 1-1/8 | 1:47.20 | II |
| 1982 | Hush Dear | 4 | Eric Beitia | J. Elliott Burch | C. V. Whitney | 1-1/8 | 1:47.40 | II |
| 1982 | If Winter Comes | 4 | Eric Beitia | Mary Cotter | E. W. Clucas Jr. | 1-1/8 | 1:47.40 | II |
| 1981 | De La Rose | 3 | Eddie Maple | Woody Stephens | Henryk de Kwiatkowski | 1-1/8 | 1:50.60 | II |
| 1980 | Just A Game | 4 | Don Brumfield | David A. Whiteley | P. Brant & J. Allen | 1-1/8 | 1:49.00 | II |
| 1979 | Pearl Necklace | 5 | Jeffrey Fell | Roger Laurin | Reginald N. Webster | 1-1/8 | 1:48.80 | II |
| 1978 | Waya | 4 | Angel Cordero, Jr. | Angel Penna, Sr. | Daniel Wildenstein | 1-1/8 | 1:45.40 | II |
| 1977 | Javamine | 4 | Angel Cordero, Jr. | MacKenzie Miller | Cragwood Stables | 1-1/8 | 1:48.40 | II |
| 1976 | Glowing Tribute | 3 | Ron Turcotte | J. Elliott Burch | Rokeby Stable | 1-1/8 | 1:47.60 | II |
| 1975 | Heloise | 4 | Michael Venezia | John A. Nerud | Tartan Stable | 1-1/8 | 1:47.40 | II |
| 1974 | Fairway Flyer | 5 | Eddie Belmonte | H. Allen Jerkens | William Floyd | 1-1/8 | 1:47.20 | II |
| 1973 | Lightning Lucy | 3 | Jorge Velasquez | John Rigione | Vee-Nine Stable | 1-1/8 | 1:46.60 | II |
| 1973 | Cathy Baby | 4 | Eddie Belmonte | William Corbellini | Mereworth Farm | 1-1/8 | 1:46.80 | II |
| 1972 | Blessing Angelica | 4 | Eddie Belmonte | H. Allen Jerkens | Hobeau Farm | 1-1/8 | 1:49.80 | |
| 1971 | Shuvee | 5 | Ron Turcotte | Willard C. Freeman | Anne Minor Stone | 1-1/8 | 1:50.60 | |
| 1970 | Shuvee | 4 | Ron Turcotte | Willard C. Freeman | Anne Minor Stone | 1-1/8 | 1:49.60 | |
| 1969 | Gamely | 5 | Eddie Belmonte | James W. Maloney | William Haggin Perry | 1-1/8 | 1:49.60 | |
| 1968 | Green Glade * | 4 | Kenneth Knapp | J. Elliott Burch | Rokeby Stable | 1-1/8 | 1:49.60 | |
| 1967 | Prides Profile | 4 | Manuel Ycaza | J. Elliott Burch | Rokeby Stable | 1-1/8 | 1:49.60 | |
| 1966 | Open Fire | 5 | Frank Lovato | Virgil W. Raines | Brandywine Stable | 1-1/8 | 1:48.80 | |
| 1965 | Steeple Jill | 4 | John Ruane | Virgil W. Raines | George D. Widener, Jr. | 1-1/8 | 1:49.60 | |
| 1964 | Prodana Neviesta | 4 | Heliodoro Gustines | Bert Mulholland | Mrs. Laudy Lawrence | 1-1/8 | 1:50.60 | |
| 1963 | Frimanaha | 6 | Johnny Sellers | Edward A. Neloy | Warner L. Jones, Jr. | 1-1/8 | 1:50.00 | |
| 1962 | Waltz Song | 4 | Sheridan Mellon | Thomas F. White | Thomas F. White | 1-1/8 | 1:49.20 | |
| 1961 | Craftiness | 6 | Bobby Ussery | Jim McGee | Frank J. Viggiani | 1-1/8 | 1:49.60 | |
| 1960 | Tempted | 5 | Eldon Nelson | Henry S. Clark | Mooring Stable | 1-1/8 | 1:51.40 | |
| 1959 | Tempted | 4 | Eldon Nelson | Henry S. Clark | Mooring Stable | 1-1/8 | 1:50.40 | |
| 1958 | Searching | 6 | Bill Hartack | Hirsch Jacobs | Ethel D. Jacobs | 1-1/8 | 1:52.20 | |
| 1957 | Pardala | 4 | Hedley Woodhouse | Hugh L. Fontaine | D and H Stable | 1-1/8 | 1:53.00 | |
| 1956 | Searching | 4 | Conn McCreary | Hirsch Jacobs | Ethel D. Jacobs | 1-1/8 | 1:52.00 | |
| 1955 | Misty Morn | 3 | Ted Atkinson | Jim Fitzsimmons | Wheatley Stable | 1-1/8 | 1:51.20 | |
| 1954 | Lavender Hill | 5 | Conn McCreary | Thomas W. Kelley | Mrs. Charles Silver | 1-1/8 | 1:52.60 | |
| 1953 | Sabette | 3 | Jesse Higley | Jim Fitzsimmons | Belair Stud | 1-1/8 | 1:52.60 | |
| 1952 | Busanda | 3 | Ted Atkinson | James Fitzsimmons | Ogden Phipps | 1-1/8 | 1:53.40 | |
| 1951 | Vulcania | 3 | Robert Bernhardt | Jim Fitzsimmons | Belair Stud | 1-1/8 | 1:52.60 | |
| 1950 | Ouija | 3 | William Boland | Preston M. Burch | Brookmeade Stable | 1-1/8 | 1:51.60 | |
| 1949 | Spats | 4 | Ted Atkinson | Not found | Mrs. Tilyou Christopher | 1-1/8 | 1:52.40 | |
| 1948 | Carolyn A. | 4 | Eddie Arcaro | James P. Conway | Mrs. Ben F. Whitaker | 1-1/8 | 1:50.80 | |
| 1947 | Miss Grillo | 5 | Conn McCreary | Horatio Luro | Mill River Stable | 1-1/8 | 1:50.40 | |
| 1946 | Miss Grillo | 4 | Conn McCreary | Horatio Luro | Mill River Stable | 1-1/8 | 1:50.20 | |
| 1945 | Surosa | 3 | Albert Snider | Richard E. Handlen | Foxcatcher Farm | 1-1/8 | 1:50.80 | |
| 1944 | Whirlabout | 3 | Herb Lindberg | Graceton Philpot | Louis B. Mayer | 1-1/8 | 1:50.20 | |
| 1943 | Bonnet Ann | 4 | Leon Haas | Hugh L. Fontaine | Brookmeade Stable | 1-1/8 | 1:50.00 | |
| 1942 | Pomayya | 4 | Alfred Robertson | Hugh L. Fontaine | Brookmeade Stable | 1-1/8 | 1:53.00 | |
| 1941 | Rosetown | 4 | Johnny Longden | Bert Mulholland | George D. Widener, Jr. | 1-1/8 | 1:53.40 | |
| 1940 | Piquet | 3 | Eddie Arcaro | John M. Gaver, Sr. | Greentree Stable | 1-1/8 | 1:52.00 | |
| 1939 | War Regalia | 3 | Don Meade | Preston M. Burch | Mrs. Walter M. Jeffords | 1-1/8 | 1:52.20 |
* 1968 - Gamely won the race but was disqualified.
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