For three-year-olds. Held two weeks after the Kentucky Derby at Pimlico Race Course in Baltimore. Inaugurated 1873. Note that the 1918 race was held over two divisions. Originally run at 11/2 miles (1873-88), then at 11/4 miles (1889), 11/2 miles (1890), 11/16 miles (1894-1900), 1 mile & 70 yards (1901-07), 11/16 miles (1908), 1 mile (1909-1910), 11/8 miles (1911-24), and the present 13/16 miles since 1925.
Trainers with most wins: Robert W. Walden (7); T.J. Healey and D. Wayne Lukas (5); Bob Baffert, Sunny Jim Fitzsimmons and Jimmy Jones (4); J. Whalen (3).
Jockeys with most wins: Eddie Arcaro (6); Pat Day (5); G. Barbee, Bill Hartack and Lloyd Hughes (3).
Winning fillies: Flocarline (1903), Whimsical (1906), Rhine Maiden (1915) and Nellie Morse (1924).
| Year | Winner (Margin) | Time | Jockey | Trainer | 2nd place | 3rd place |
|---|---|---|---|---|---|---|
| 1873 | Survivor (10) | 2:43 | G. Barbee | A.D. Pryor | John Boulger | Artist |
| 1874 | Culpepper (3/4) | 2:561/2 | W. Donohue | H. Gaffney | King Amadeus | Scratch |
| 1875 | Tom Ochiltree (2) | 2:431/2 | L. Hughes | R.W. Walden | Viator | Bay Final |
| 1876 | Shirley (4) | 2:443/4 | G. Barbee | W. Brown | Rappahannock | Compliment |
| 1877 | Cloverbrook (2) | 2:451/2 | C. Holloway | J. Walden | Bombast | Lucifer |
| 1878 | Duke of Magenta (2) | 2:413/4 | C. Holloway | R.W. Walden | Bayard | Albert |
| 1879 | Harold (1) | 2:401/2 | L. Hughes | R.W. Walden | Jericho | Rochester |
| 1880 | Grenada (3/4) | 2:401/2 | L. Hughes | R.W. Walden | Oden | Emily F. |
| 1881 | Saunterer (1/2) | 2:401/2 | T. Costello | R.W. Walden | Compensation | Baltic |
| 1882 | Vanguard (nk) | 2:441/2 | T. Costello | R.W. Walden | Heck | Col. Watson |
| 1883 | Jacobus (4) | 2:421/2 | G. Barbee | R. Dwyer | Parnell | (2-horse race) |
| 1884 | Knight of Ellerslie (2) | 2:391/2 | S. Fisher | T.B. Doswell | Welcher | (2-horse race) |
| 1885 | Tecumseh (2) | 2:49 | Jim McLaughlin | C. Littlefield | Wickham | John C. |
| 1886 | The Bard (3) | 2:45 | S. Fisher | J. Huggins | Eurus | Elkwood |
| 1887 | Dunboyne (1) | 2:391/2 | W. Donohue | W. Jennings | Mahoney | Raymond |
| 1888 | Refund (3) | 2:49 | F. Littlefield | R.W. Walden | Bertha B.* | Glendale |
| 1889 | Buddhist (8) | 2:171/2 | W. Anderson | J. Rogers | Japhet | (2-horse race) |
| 1890 | Montague (3) | 2:363/4 | W. Martin | E. Feakes | Philosophy | Barrister |
| 1891-93 Not held | ||||||
| 1894 | Assignee (3) | 1:491/4 | F. Taral | W. Lakeland | Potentate | Ed Kearney |
| 1895 | Belmar (1) | 1:501/2 | F. Taral | E. Feakes | April Fool | Sue Kittie |
| 1896 | Margrave (1) | 1:51 | H. Griffin | Byron McClelland | Hamilton II | Intermission |
| 1897 | Paul Kauvar (11/2) | 1:511/4 | T. Thorpe | T.P. Hayes | Elkins | On Deck |
| 1898 | Sly Fox (2) | 1:493/4 | W. Simms | H. Campbell | The Huguenot | Nuto |
| 1899 | Half Time (1) | 1:47 | R. Clawson | F. McCabe | Filigrane | Lackland |
| 1900 | Hindus (hd) | 1:482/5 | H. Spencer | J.H. Morris | Sarmatian | Ten Candles |
| 1901 | The Parader (2) | 1:471/5 | F. Landry | T.J. Healey | Sadie S. | Dr. Barlow |
| 1902 | Old England (ns) | 1:454/5 | L. Jackson | G.B. Morris | Maj. Daingerfield | Namtor |
| 1903 | Flocarline (1/2) | 1:444/5 | W. Gannon | H.C. Riddle | Mackey Dwyer | Rightful |
| 1904 | Bryn Mawr (1) | 1:441/5 | E. Hildebrand | W.F. Presgrave | Wotan | Dolly Spanker |
| 1905 | Cairngorm (hd) | 1:454/5 | W. Davis | A.J. Joyner | Kiamesha | Coy Maid |
| 1906 | Whimsical (4) | 1:45 | Walter Miller | T.J. Gaynor | Content | Larabie |
| 1907 | Don Enrique (1) | 1:452/5 | G. Mountain | J. Whalen | Ethon | Zambesi |
| 1908 | Royal Tourist (4) | 1:462/5 | Eddie Dugan | A.J. Joyner | Live Wire | Robert Cooper |
| 1909 | Effendi (1) | 1:394/5 | Willie Doyle | F.C. Frisbie | Fashion Plate | Hill Top |
| 1910 | Layminster (1/2) | 1:403/5 | R. Estep | J.S. Healy | Dalhousie | Sager |
| 1911 | Watervale (1) | 1:51 | Eddie Dugan | J. Whalen | Zeus | The Nigger |
| 1912 | Colonel Holloway (5) | 1:563/5 | C. Turner | D. Woodford | Bwana Tumbo | Tipsand |
| 1913 | Buskin (nk) | 1:532/5 | James Butwell | J. Whalen | Kleburne | Barnegat |
| 1914 | Holiday (3/4) | 1:534/5 | A. Schuttinger | J.S. Healy | Brave Cunarder | Defendum |
| 1915 | Rhine Maiden (11/2) | 1:58 | Douglas Hoffman | F. Devers | Half Rock | Runes |
| 1916 | Damrosch (11/2) | 1:544/5 | Linus McAtee | A.G. Weston | Greenwood | Achievement |
| 1917 | Kalitan (2) | 1:542/5 | E. Haynes | Bill Hurley | Al M. Dick | Kentucky Boy |
| 1918 | War Cloud (3/4) | 1:533/5 | Johnny Loftus | W.B. Jennings | Sunny Slope | Lanius |
| 1918 | Jack Hare Jr (2) | 1:532/5 | Charles Peak | F.D. Weir | The Porter | Kate Bright |
| 1919 | SIR BARTON (4) | 1:53 | Johnny Loftus | H. Guy Bedwell | Eternal | Sweep On |
| 1920 | Man o' War (11/2) | 1:513/5 | Clarence Kummer | L. Feustel | Upset | Wildair |
| 1921 | Broomspun (3/4) | 1:541/5 | F. Coltiletti | James Rowe Sr. | Polly Ann | Jeg |
| 1922 | Pillory (hd) | 1:513/5 | L. Morris | Thomas Healey | Hea | June Grass |
| 1923 | Vigil (11/4) | 1:533/5 | B. Marinelli | Thomas Healey | General Thatcher | Rialto |
| 1924 | Nellie Morse (11/2) | 1:571/5 | John Merimee | A.B. Gordon | Transmute | Mad Play |
| 1925 | Coventry (4) | 1:59 | Clarence Kummer | William Duke | Backbone | Almadel |
| 1926 | Display (hd) | 1:594/5 | John Maiben | Thomas Healey | Blondin | Mars |
| 1927 | Bostonian (1/2) | 2:013/5 | Whitey Abel | Fred Hopkins | Sir Harry | Whiskery |
| 1928 | Victorian (ns) | 2:001/5 | Sonny Workman | James Rowe Jr. | Toro | Solace |
| 1929 | Dr. Freeland (1) | 2:013/5 | Louis Schaefer | Thomas Healey | Minotaur | African |
| 1930 | GALLANT FOX (3/4) | 2:003/5 | Earl Sande | Jim Fitzsimmons | Crack Brigade | Snowflake |
| 1931 | Mate (11/2) | 1:59 | George Ellis | J.W. Healy | Twenty Grand | Ladder |
| 1932 | Burgoo King (hd) | 1:594/5 | Eugene James | Dick Thompson | Tick On | Boatswain |
| 1933 | Head Play (4) | 2:02 | Charley Kurtsinger | Thomas Hayes | Ladysman | Utopian |
| 1934 | High Quest (ns) | 1:581/5 | Robert Jones | Bob Smith | Cavalcade | Discovery |
| 1935 | OMAHA (6) | 1:582/5 | Willie Saunders | Jim Fitzsimmons | Firethorn | Psychic Bid |
| 1936 | Bold Venture (ns) | 1:59 | George Woolf | Max Hirsch | Granville | Jean Bart |
| 1937 | WAR ADMIRAL (hd) | 1:582/5 | Charley Kurtsinger | George Conway | Pompoon | Flying Scot |
| 1938 | Dauber (7) | 1:594/5 | Maurice Peters | Dick Handlen | Cravat | Menow |
| 1939 | Challedon (11/4) | 1:594/5 | George Seabo | Louis Schaefer | Gilded Knight | Volitant |
| 1940 | Bimelech (3) | 1:583/5 | F.A. Smith | Bill Hurley | Mioland | Gallahadion |
| 1941 | WHIRLAWAY (51/2) | 1:584/5 | Eddie Arcaro | Ben Jones | King Cole | Our Boots |
| 1942 | Alsab (1) | 1:57 | Basil James | Sarge Swenke | Requested & Sun Again (dead heat) | |
| 1943 | COUNT FLEET (8) | 1:572/5 | Johnny Longden | Don Cameron | Blue Swords | Vincentive |
| 1944 | Pensive (3/4) | 1:591/5 | Conn McCreary | Ben Jones | Platter | Stir Up |
| 1945 | Polynesian (21/2) | 1:584/5 | W.D. Wright | Morris Dixon | Hoop Jr. | Darby Dieppe |
| 1946 | ASSAULT (nk) | 2:012/5 | Warren Mehrtens | Max Hirsch | Lord Boswell | Hampden |
| 1947 | Faultless (11/4) | 1:59 | Doug Dodson | Jimmy Jones | On Trust | Phalanx |
| 1948 | CITATION (51/2) | 2:022/5 | Eddie Arcaro | Jimmy Jones | Vulcan's Forge | Bovard |
| 1949 | Capot (hd) | 1:56 | Ted Atkinson | J.M. Gaver | Palestinian | Noble Impulse |
| 1950 | Hill Prince (5) | 1:591/5 | Eddie Arcaro | Casey Hayes | Middleground | Dooly |
| 1951 | Bold (7) | 1:562/5 | Eddie Arcaro | Preston Burch | Counterpoint | Alerted |
| 1952 | Blue Man (31/2) | 1:572/5 | Conn McCreary | Woody Stephens | Jampol | One Count |
| 1953 | Native Dancer (nk) | 1:574/5 | Eric Guerin | Bill Winfrey | Jamie K. | Royal Bay Gem |
| 1954 | Hasty Road (nk) | 1:572/5 | Johnny Adams | Harry Trotsek | Correlation | Hasseyampa |
| 1955 | Nashua (1) | 1:543/5 | Eddie Arcaro | Jim Fitzsimmons | Saratoga | Traffic Judge |
| 1956 | Fabius (3/4) | 1:582/5 | Bill Hartack | Jimmy Jones | Needles | No Regrets |
| 1957 | Bold Ruler (2) | 1:561/5 | Eddie Arcaro | Jim Fitzsimmons | Iron Liege | Inside Tract |
| 1958 | Tim Tam (11/2) | 1:571/5 | Ismael Valenzuela | Jimmy Jones | Lincoln Road | Gone Fishin' |
| 1959 | Royal Orbit (4) | 1:57 | William Harmatz | R. Cornell | Sword Dancer | Dunce |
| 1960 | Bally Ache (4) | 1:573/5 | Bobby Ussery | Jimmy Pitt | Victoria Park | Celtic Ash |
| 1961 | Carry Back (3/4) | 1:573/5 | Johnny Sellers | Jack Price | Globemaster | Crozier |
| 1962 | Greek Money (ns) | 1:561/5 | John Rotz | V.W. Raines | Ridan | Roman Line |
| 1963 | Candy Spots (31/2) | 1:561/5 | Bill Shoemaker | Mesh Tenney | Chateaugay | Never Bend |
| 1964 | Northern Dancer (21/4) | 1:564/5 | Bill Hartack | Horatio Luro | The Scoundrel | Hill Rise |
| 1965 | Tom Rolfe (nk) | 1:561/5 | Ron Turcotte | Frank Whiteley | Dapper Dan | Hail To All |
| 1966 | Kauai King (13/4) | 1:552/5 | Don Brumfield | Henry Forrest | Stupendous | Amberoid |
| 1967 | Damascus (21/4) | 1:551/5 | Bill Shoemaker | Frank Whiteley | In Reality | Proud Clarion |
| 1968 | Forward Pass (6) | 1:564/5 | Ismael Valenzuela | Henry Forrest | Out Of the Way | Nodouble |
| 1969 | Majestic Prince (hd) | 1:553/5 | Bill Hartack | Johnny Longden | Arts and Letters | Jay Ray |
| 1970 | Personality (nk) | 1:561/5 | Eddie Belmonte | John Jacobs | My Dad George | Silent Screen |
| 1971 | Canonero II (11/2) | 1:54 | Gustavo Avila | Juan Arias | Eastern Fleet | Jim French |
| 1972 | Bee Bee Bee (11/4) | 1:553/5 | Eldon Nelson | Red Carroll | No Le Hace | Key To The Mint |
| 1973 | SECRETARIAT (21/2) | 1:542/5 | Ron Turcotte | Lucien Laurin | Sham | Our Native |
| 1974 | Little Current (7) | 1:543/5 | Miguel Rivera | Lou Rondinello | Neapolitan Way | Cannonade |
| 1975 | Master Derby (1) | 1:562/5 | Darrel McHargue | Smiley Adams | Foolish Pleasure | Diabolo |
| 1976 | Elocutionist (31/2) | 1:55 | John Lively | Paul Adwell | Play The Red | Bold Forbes |
| 1977 | SEATTLE SLEW (11/2) | 1:542/5 | Jean Cruguet | Billy Turner | Iron Constitution | Run Dusty Run |
| 1978 | AFFIRMED (nk) | 1:542/5 | Steve Cauthen | Laz Barrera | Alydar | Believe It |
| 1979 | Spectacular Bid (31/2) | 1:541/5 | Ron Franklin | Bud Delp | Golden Act | Screen King |
| 1980 | Codex (43/4) | 1:541/5 | Angel Cordero Jr. | D. Wayne Lukas | Genuine Risk | Colonel Moran |
| 1981 | Pleasant Colony (1) | 1:543/5 | Jorge Velasquez | John Campo | Bold Ego | Paristo |
| 1982 | Aloma's Ruler (1/2) | 1:552/5 | Jack Kaenel | John Lenzini Jr. | Linkage | Cut Away |
| 1983 | Deputed Testamony (23/4) | 1:552/5 | Donald Miller Jr. | Bill Boniface | Desert Wine | High Honors |
| 1984 | Gate Dancer (11/2) | 1:533/5 | Angel Cordero Jr. | Jack Van Berg | Play On | Fight Over |
| 1985 | Tank's Prospect (hd) | 1:532/5 | Pat Day | D. Wayne Lukas | Chief's Crown | Eternal Prince |
| 1986 | Snow Chief (4) | 1:544/5 | Alex Solis | Melvin Stute | Ferdinand | Broad Brush |
| 1987 | Alysheba (1/2) | 1:554/5 | Chris McCarron | Jack Van Berg | Bet Twice | Cryptoclearance |
| 1988 | Risen Star (11/4) | 1:561/5 | E. Delahoussaye | Louie Roussel III | Brian's Time | Winning Colors |
| 1989 | Sunday Silence (ns) | 1:534/5 | Pat Valenzuela | Chas. Whittingham | Easy Goer | Rock Point |
| 1990 | Summer Squall (21/4) | 1:533/5 | Pat Day | Neil Howard | Unbridled | Mister Frisky |
| 1991 | Hansel (7) | 1:54 | Jerry Bailey | Frank Brothers | Corporate Report | Mane Minister |
| 1992 | Pine Bluff (3/4) | 1:553/5 | Chris McCarron | Tom Bohannan | Alydeed | Casual Lies |
| 1993 | Prairie Bayou (1/2) | 1:563/5 | Mike Smith | Tom Bohannan | Cherokee Run | El Bakan |
| 1994 | Tabasco Cat (3/4) | 1:562/5 | Pat Day | D. Wayne Lukas | Go For Gin | Concern |
| 1995 | Timber Country (1/2 | 1:542/5 | Pat Day | D. Wayne Lukas | Oliver's Twist | Thunder Gulch |
| 1996 | Louis Quatorze (31/4) | 1:532/5 | Pat Day | Nick Zito | Skip Away | Editor's Note |
| 1997 | Silver Charm (hd) | 1:542/5 | Gary Stevens | Bob Baffert | Free House | Captain Bodgit |
| 1998 | Real Quiet (21/4) | 1:544/5 | Kent Desormeaux | Bob Baffert | Victory Gallop | Classic Cat |
| 1999 | Charismatic (11/2) | 1:551/5 | Chris Antley | D. Wayne Lukas | Menifee | Badge |
| 2000 | Red Bullet (33/4) | 1:56 | Jerry Bailey | Joe Orseno | Fusaichi Pegasus | Impeachment |
| 2001 | Point Given (21/4) | 1:552/5 | Gary Stevens | Bob Baffert | A P Valentine | Congaree |
| 2002 | War Emblem (3/4) | 1:561/5 | Victor Espinoza | Bob Baffert | Magic Weisner | Proud Citizen |
| 2003 | Funny Cide (93/4) | 1:553/5 | Jose Santos | Barclay Tagg | Midway Road | Scrimshaw |
| 2004 | Smarty Jones (111/2) | 1:552/5 | Stewart Elliott | John Servis | Rock Hard Ten | Eddington |
| 2005 | Afleet Alex (43/4) | 1:551/25 | Jeremy Rose | Tim Ritchey | Scrappy T | Giacomo |
| 2006 | Bernardini (51/4) | 154.65 | J. J. Castellano | Thomas Albertrani | Sweetnorthernsaint | Hemingway's Key |
| 2007 | Curlin (head) | 153.46 | Robby Albarado | Steve Asmussen | Street Sense | Hard Spun |
| 2008 | Big Brown (51/4) | 154.80 | Kent Desormeaux | Richard E. Dutrow, Jr. | Macho Again | Icabad Crane |
| Kentucky Derby | The Triple Crown | Belmont Stakes |