May 10, 1842: Fashion, representing the North, competed against Boston, representing the South, in a match race at Union Course. Described by contemporaries as the best race ever run in America, with $20,000 put up on each side, the match was won by Fashion before a crowd estimated between 50,000 and 70,000.
May 10, 1910: George Woolf, namesake of a jockey’s award given annually by Santa Anita Park, was born in Cardston, Alberta.
May 10, 1919: Sir Barton won the Kentucky Derby after being winless in six tries. Four days later, on May 14, he won the Preakness Stakes, and on June 11, he became the first Triple Crown winner after capturing the Belmont Stakes.
May 11, 1888: Trainer Robert Walden set the record for the most number of Preakness winners—seven—when he sent Refund to victory.
May 11, 1892: African American jockey Alonzo Clayton, age 15, became the youngest rider to win the Kentucky Derby when he guided Azra to victory in the 18th running of the Derby.
May 11, 1935: Trainer “Sunny Jim” Fitzsimmons sent a two-year-old colt, White Cockade, to victory in the Youthful Stakes at Jamaica, giving his 26-year-old owner, Ogden Phipps, his first stakes win ever.
May 12, 1909: The Preakness Stakes was held in Maryland after 16 runnings in New York. As part of the celebration that marked the return of the Preakness, the colors of the race’s winner were painted onto the ornamental weathervane at Pimlico Racecourse for the first time.
May 12, 1917: Omar Khayyam became the first foreign-bred horse to win the Kentucky Derby. He was bred in England.
May 12, 1924: Nellie Morse became the fourth and last filly to win the Preakness Stakes. Other fillies to win the Preakness were Flocarline (1903); Whimsical (1906); and Rhine Maiden (1915).
May 12, 1936: Jockey Ralph Neves was involved in a racing accident at Bay Meadows and erroneously pronounced dead. He was later revived at the morgue and he returned to the racetrack the same day. He was ordered to sit out the remainder of the racing card and so missed only a half-day of work because of his “death.”
May 12, 1990: D. Wayne Lukas became the first trainer to top $100 million in purses when he sent Calumet Farm’s Criminal Type to win the Pimlico Special at Pimlico Racecourse.
May 13, 1845: The Great Sectional Match, the North versus the South, was run at Union Course in New York. Fashion, representing the North, raced against the South’s Peytona in a match race won by Peytona. Three years earlier, Fashion had defeated Boston, who represented the South, in another North-South rivalry.
May 13, 1891: Kingman, the only African American-owned horse to win the Derby, did so with jockey Isaac Murphy in the irons. Kingman was owned and trained by African American Dudley Allen. The win gave jockey Isaac Murphy back-to-back Derby victories and made him the first jockey to win three Derbies.
May 13, 1939: Louis Schaefer became the first person to have ridden and trained a Preakness Stakes winner after he saddled Challedon to victory. Schaefer won the 1929 Preakness as a jockey, riding Dr. Freeland. Schaefer’s double was replicated by jockey-turned-trainer John Longden, who rode Count Fleet in the 1943 Preakness and trained Majestic Prince to win the race in 1969.
May 13, 1973: Secretariat worked five furlongs in :57 2/5 at Pimlico Racecourse in preparation for the May 19 Preakness Stakes. He was eased after completing his workout distance, but still ran six furlongs in 1:10.
May 14, 1989: E.P. Taylor, owner of Windfields Farms and breeder of Northern Dancer, died at age 88.
May 14, 2000: Arlington Park in Arlington Heights, Ill., re-opened its gates to racing after being closed for two years, welcoming a crowd of 35,273.
May 14, 2010: Retired jockey Gwen Jocson guided home Honor in Peace to win the first-ever Lady Legends for the Cure race at Pimlico.
May 15, 1918: Two horses—War Cloud and Jack Hare Jr.—were declared the winner of the Preakness Stakes, not because of a dead heat, but because the race was run in two divisions.
May 15, 1952: John Longden gained his 4,000th victory, riding at Hollywood Park.
May 15, 1954: Nashua won his first race, running 4 ½ furlongs over a straightaway at Belmont Park.
May 15, 1993: Genuine Risk, the second of three fillies to have won the Kentucky Derby since it began in 1875, gave birth to her first foal after 13 years of failed attempts and miscarriages. The foal, a son of Rahy, was named Genuine Reward.
May 15, 1999: Lee Chang Ferrell, a patron in the Pimlico infield, jumped onto the track in midstretch and interfered with the running of the Maryland Breeders’ Cup Handicap. The race winner, Yes It’s True, avoided the trouble, but wagers on fifth-place finisher Artax were refunded due to the incident. Later that day, Charismatic, winner of the Kentucky Derby, took the Preakness Stakes before a record crowd of 100,311.
May 15, 2004: Smarty Jones won the Preakness Stakes by 11 ½ lengths, the largest winning margin in the 129-year history of the event.
May 16, 1884: Buchanan became the first maiden to win the Kentucky Derby. Only two other maiden horses have gone on to win the Run for the Roses: Sir Barton in 1919, and Brokers Tip in 1933.
May 16, 1925: The first network radio broadcast of the Kentucky Derby aired from WHAS in Louisville.
May 16, 1979: Gary Stevens rode his first career winner, named Lil Star, trained by his father, Ron Stevens, at Les Bois Park.
May 16, 1998: Bob Baffert became the first person to train Kentucky Derby and Preakness Stakes winners in successive years. In 1997, Baffert won the Derby and Preakness with Silver Charm; the following year, he won with Real Quiet.
May 16, 1998: During Preakness Stakes Day at Pimlico Racecourse, a transformer went down at 1:00 p.m., causing a power failure in the grandstand. With temperatures in the 90s, the facility had no operating air-conditioning, lights, closed-circuit television, public address system, elevators, escalators or betting windows. A record crowd of 91,122 was on hand and an estimated $1.5 million in on-track handle was lost.
May 16, 2009: Rachel Alexandra became just the fifth filly to win the Preakness Stakes, and the first since Nellie Morse in 1924. Rachel Alexandra held off the late rush of Kentucky Derby victor Mine That Bird to secure the win.
May 17, 1875: America’s oldest continuously held sporting event, the Kentucky Derby, was first run. The race was won by Aristides, who was ridden and trained by African Americans Oliver Lewis and Ansel Williamson, respectively. The day marked the opening of Churchill Downs; an estimated 10,000 spectators witnessed the first Derby.
May 17, 1881: James Rowe Sr., then age 24, became the youngest trainer to saddle a Kentucky Derby winner after Hindoo took the 7th Derby for his owners, brothers Phil and Mike Dwyer, both notorious gamblers.
May 17, 1915: Rhine Maiden, in winning the Preakness Stakes, produced the only Kentucky Derby-Preakness wins by fillies in the same year. The 1915 Derby was won by Regret, who did not compete in the Preakness.
May 17, 1930: Two-year-old Equipoise gave owner C.V. Whitney his first stakes victory when he captured the Keene Memorial Stakes at Belmont Park at odds of 3-5.
May 17, 1947: Seabiscuit, owned by Charles S. Howard, succumbed to a heart attack at Ridgewood Ranch in Willits, Calif. He was 14.
May 17, 1976: Sixteen-year-old Steve Cauthen rode his first winner, Thomas Bischoff-trained Red Pipe, in the eighth race at River Downs. By the end of his first year of apprenticeship, Cauthen had won 240 races from 1,170 mounts and $1.2 million in purses.
May 18, 1931: Fifteen-year-old Eddie Arcaro rode his first race, finishing sixth, at Bainbridge Park, Ohio. At year’s end, he remained winless after 36 tries.
May 18, 1935: The Seagram family won the Queen’s Plate stakes (then called the King’s Plate), a record 20th time. From 1891-1898, the Seagrams’ horses won the Plate every year.
May 18, 1957: Eddie Arcaro set the record for most number of Preakness Stakes wins by a jockey, six, when he rode Bold Ruler to victory for Wheatley Stable.
May 18, 1968: Judy Johnson became the first female trainer to saddle a horse for the Preakness Stakes. Her horse, Sir Beau, finished seventh in a field of 10.
May 18, 1968: Calumet Farm set the record for most number of wins in the Preakness Stakes by an owner, seven, when Forward Pass won the race by six lengths.
May 18, 1985: Patricia Cooksey became the first female jockey to compete in the Preakness Stakes. Her mount, Tajawa, finished sixth in a field of 11.
May 18, 1996: Jockey Pat Day won his third consecutive Preakness Stakes and his fifth Preakness overall, after riding Louis Quatorze to victory. The win, for trainer Nick Zito, snapped the Triple Crown race win-streak of trainer D. Wayne Lukas, which had run to six, beginning with the 1994 Preakness, won by Tabasco Cat.
May 18, 1998: Trainer Aimee Hall saddled four winners from five starters at Suffolk Downs, with all of the winners being ridden by her husband, Jose Caraballo. The wins are believed to be the first involving a married couple as jockey and trainer.
May 19, 1961: Jockey Bill Shoemaker notched his 4,000th career win aboard Guaranteeya at Hollywood Park.
May 19, 1964: Jockey Laffit Pincay Jr. won his first race, aboard Huelen, riding at Presidente Remon in Panama.
May 19, 1973: Secretariat’s winning performance in the Preakness Stakes was marred by a controversy over the timing of the race. The original teletimer time was 1:55 for the 1 3/16-mile race; Pimlico amended it to 1:54 2/5 two days later.
May 19, 1999: Secretariat was honored as the 35th greatest athlete of the 20th Century by ESPN’s SportsCentury, a series of programs profiling the top athletes of the past 100 years. Secretariat was the only non-human to make the top 50.
May 20, 1916: In an unprecedented sweep, Mandarin, Gala Water and Gala Day finished first, second and third, respectively, in the King’s Plate at Woodbine for their owner, distiller Joseph Emm Seagram. Three days later, Mandarin and Gala Water again finished one-two, this time in the Breeders’ Stakes.
May 20, 1941: Seventeen days after his Kentucky Derby win and 10 days after his Preakness victory, Whirlaway raced against older horses for the first time. Carrying 108 pounds, Whirlaway defeated his four rivals in the Henry of Navarre Purse at Belmont Park.
May 20, 1954: At odds of 13-1, Rex Ellsworth’s two-year-old colt Swaps won his maiden race by three lengths at Hollywood Park.
May 20, 1973: Having won the Kentucky Derby and Preakness Stakes, Secretariat shipped from Pimlico to New York in preparation for the Belmont Stakes, final jewel in the Triple Crown.
May 20, 1977: Two-year-old John Henry won his first start ever, a four-furlong maiden race at Jefferson Downs, by a nose. When he was retired in 1984, the gelding had 39 wins, 15 seconds and nine thirds from 83 starts, seven Eclipse Awards and earnings of $6,597,947.
May 20, 2006: Barbaro, the 2006 Kentucky Derby winner, suffered a life-threatening right hind leg injury shortly after the start of the Preakness Stakes.
May 21, 1978: John Henry made his first start for Dotsam Stable, winning a $25,000 claiming race at Aqueduct.
May 21, 1992: Jockey Gary Stevens registered his 3,000th winner in the fifth race at Hollywood Park, aboard Sharp Event.
May 21, 2005: A record crowd of 115,318 witnessed Afleet Alex stumble badly at the quarter-pole, regain his balance under jockey Jeremy Rose and win the Preakness Stakes over Scrappy T by 4 ¾ lengths.
May 21, 2006: Dr. Dean Richardson and a team of doctors operated on Barbaro the day after he suffered a life threatening injury in the Preakness. Richardson fused Barbaro’s right-hind leg with 27 screws and a metal plate, then fitted his shattered leg into a cast.
May 22, 1974: Locust Hill Farm’s Ruffian won her first start, a maiden race for two-year-old fillies, by 15 lengths at Belmont Park. Sent off at odds of 4-1, Ruffian completed the 5 1/2 furlongs in 1:03.
May 23, 1936: Rushaway, ridden by John Longden, won his second derby in as many days, taking the 1 1/4-mile Latonia Derby at Latonia in Covington, Ky. Rushaway had won the 1 1/8-mile Illinois Derby, run at Aurora, outside Chicago, the previous day.
May 23, 1992: Jockey Jacinto Vasquez had his 5,000th career winner, aboard Susan Pixum, at Calder Racecourse.