1875 – Hal Price McGrath’s Aristides wins the first Kentucky Derby with Oliver Lewis aboard for trainer Ansel Williamson. The first Derby is run at 1 1/2 miles. 1882 – Apollo wins the Derby without having run as a 2-year-old. No other horse would accomplish that feat – “the curse of Apollo” – until Justify 136 years later. 1913 – Donerail takes the Derby at a shocking 91-1, to this day the longest odds ever for a Kentucky Derby winner. 1915 – The New Jersey-bred Regret becomes the first filly to win the Kentucky Derby. It would be 65 years until another filly would wear the roses. 1919 – Sir Barton wins the first race of his career in the Derby. Four days later, he takes the Preakness, and after a victory in the Withers, wins the Belmont to become the first horse to win the Triple Crown. 1930 – Gallant Fox wins the Derby eight days after winning the Preakness. Three weeks later, he would take the Belmont and become the second to sweep the classics, though the first to be called the Triple Crown winner. 1933 – Brokers Tip becomes the fourth and final Derby winner (all beginning with the letter “B”) for owner Col. E.R. Bradley and trainer “Derby Dick” Thompson after an infamous stretch run where Don Meade, aboard Brokers Tip, and Herb Fisher, on Head Play, pulled on each other’s saddlecloths and boots. In the end, it was Brokers Tip by nose, the first and only victory of his career. :: DRF Kentucky Derby Package: Save on PPs, Clocker Reports, Betting Strategies, and more. 1935 – Omaha, from the first crop of Gallant Fox, wins the second Derby, and eventually the second Triple Crown, in five years for Belair Stud and trainer “Sunny” Jim Fitzsimmons. 1937 – A son of Man o’ War, considered by many to be the greatest horse of all time, War Admiral dominates the Derby wire to wire for Man o’ War’s owner, Samuel D. Riddle. He would go on to be the fourth Triple Crown winner. Keeneland Library 1941 –Whirlaway (above), the popular “Mr. Longtail,” wins the Derby in his 24th start, and eighth of the season, by a record-tying eight lengths in 2:01.40, at the time the fastest Derby at 1 1/4 miles. He completed a Triple Crown sweep five weeks later in the Belmont. 1943 – In contrast to Whirlaway, Count Fleet wins the Derby in just his third start of the year, all within 18 days. He polished off his Triple Crown by a remarkable 25 lengths in the Belmont, but never raced again. 1948 – Citation dominates his Calumet stablemate Coaltown after spotting him a six-length early lead. Citation would go on to win another 13 straight starts, including a Triple Crown sweep, the last time all three classics were won by the same horse for another 25 years. 1953 – In one of the most shocking upsets in racing history, 25-1 Dark Star outlasts the undefeated 3-5 favorite Native Dancer, who suffered a horrible trip, by a rapidly diminishing head. Native Dancer would never lose again. 1955 – The California speedball Swaps outduels 2-year-old champion and East Coast stalwart Nashua in what many consider to be the coming of age for West Coast racing. Keeneland Library 1957 – In a race that featured one of the greatest crops in Thoroughbred history, including Bold Ruler, Gallant Man, and Round Table, it is little-regarded Iron Liege (above) who wins the roses after Bill Shoemaker aboard Gallant Man briefly stands up in the saddle at the sixteenth pole, likely the difference in Iron Liege’s nose victory. 1962 – Known as “The People’s Horse,” Carry Back splashes his way to victory for his colorful owner-trainer Jack Price. Carry Back won the Preakness, lost his Triple Crown bid in the Belmont, but was the toast of Paris for his foray the next year in the Prix de l’Arc de Triomphe. 1968 – Dancer’s Image becomes the first horse to be disqualified from victory in the Kentucky Derby after a post-race test showed the presence of phenylbutazone (Bute) in his system. Keeneland Library 1970 – Fifteen months after she became the first female jockey to ride in a parimutuel race in the United States, Diane Crump (above) becomes the first woman to ride in the Derby, finishing 15th on Fathom. 1973 – Secretariat takes his first steps to immortality with a 2 1/2-length victory over archrival Sham. His clocking of 1:59 2/5 was the first sub-2:00 Derby and to this day remains the standard for the race. “Big Red” would go on to set records in the Preakness and Belmont as well to become the first Triple Crown winner in 25 years. 1974 – A record crowd of 163,628 jams Churchill for the Centennial Derby, and the starting gate is at capacity as well. A field of 23, the largest ever for the Derby, competes, and Cannonade wins the cavalry charge, causing Churchill to consider a cap on field size in the future. 1977 – Undefeated Seattle Slew runs the Derby field off its feet and goes on to do the same in the Preakness and Belmont to become to first horse to win the Triple Crown without a loss. 1978 – Affirmed wins the first of three epic classic confrontations with Alydar, scoring by 1 1/2 lengths. The margins got smaller through the series, with Affirmed winning the Preakness by a neck and the Belmont, after a three-quarter-mile head-to-head battle, by a head to win the Triple Crown. 1980 – Somewhat dismissed at 13-1, Genuine Risk, the first filly to even run in the Derby since Silver Spoon in 1959, becomes the second filly to win the roses and the first in 65 years. 1986 – Ferdinand makes 54-year-old Bill Shoemaker and 73-year-old Charlie Whittingham the oldest jockey and trainer, respectively, to win the Kentucky Derby. 1988 – After a string of frustrating Derby losses, trainer D. Wayne Lukas wins the first of his four Kentucky Derbies with a filly, the strapping gray Winning Colors, who goes wire to wire. 1997 – A year after being denied the Derby by a dirty nose, Silver Charm gives trainer Bob Baffert his first of six Derby wins. Baffert has gone on to be the winningest Triple Crown trainer ever. John C. Engelhardt/Pat Lang Photography 2007 – Street Sense (above) becomes the first Breeders’ Cup Juvenile winner, and the first juvenile champion since Spectacular Bid in 1979, to win the Derby. Barbara D. Livingston 2015 – American Pharoah (above) gives Baffert his fourth Derby winner. He will go on to become the first Triple Crown winner in 37 years and the first and only horse to win the “Grand Slam,” the Triple Crown plus the Breeders’ Cup Classic. 2018 – Justify breaks the “Curse of Apollo,” becoming the first horse since 1882 to win the Derby after not racing as a 2-year-old. He finishes off the Triple Crown in a career that lasts just 111 days five weeks later in the Belmont. 2019 – A Derby winner is disqualified on the racetrack for the first time as the stewards, after a more than 20-minute inquiry, take down Maximum Security for interference around the quarter pole and place him 17th, making 65-1 Country House the official winner. 2020 – The COVID-19 pandemic forces the Derby to be moved to the first Saturday in September and making it the middle leg of the Triple Crown. Authentic gives Baffert his sixth Derby winner, tying him with Ben Jones. 2021 – A post-race positive for the steroid betamethasone in first-place finisher Medina Spirit denies what would have been a record seventh Derby win for Baffert. Second finisher Mandaloun is awarded the victory. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.