Macbeth II was a horse who was the winner of the 1888 Kentucky Derby He was the third gelding and one of only nine geldings to win the Kentucky Derby, with the others being Vagrant (1876), Apollo (1882), Old Rosebud (1914), Exterminator (1918), Paul Jones (1920), Clyde Van Dusen (1929), Funny Cide (2003), and Mine That Bird (2009).
Paul Jones (1917–1930) was an American Thoroughbred racehorse that was the sixth gelding to win the Kentucky Derby. Paul Jones was foaled in the same year as Man o' War, winner of the 1920 Preakness and Belmont Stakes and one of the most influential sires of the 20th century. Man o' War was not entered in the 1920 Kentucky Derby because it was thought that a race so early in the season would be too taxing for him. Upset, the only horse ever to defeat Man o' War, did make it to the Derby.
Meridian (1908–1935) was an American Thoroughbred racehorse that won the 1911 Kentucky Derby, setting a new record by running 11⁄4 miles in 2 minutes, 5 seconds. The previous record of 2:061⁄4 had been set by Lieut. Gibson in the 1900 Derby. Meridian was determined to be the historical Champion Three-Year Old and Horse of the Year of 1911.
The 1888 Kentucky Derby was the 14th running of the Kentucky Derby. The race took place on May 14, 1888. The track was labeled as fast.
The 1889 Kentucky Derby was the 15th running of the Kentucky Derby, won by Spokane. The race took place on May 9, 1889. The winning time of 2:34.50 set a new Derby record for a distance of 1+1⁄2 miles (2.4 km), and remains the Derby record for the distance This was the first Derby where $2 win wagers were available.
The 1895 Kentucky Derby was the 21st running of the Kentucky Derby. The race took place on May 6, 1895. It was the last Kentucky Derby race that was run at a distance of 1+1⁄2 miles (2.4 km). In 1896, the race was shortened to 1+1⁄4 miles (2.0 km), which has remained as the current race length.
The 1902 Kentucky Derby was the 28th running of the Kentucky Derby. The race took place on May 3, 1902. This marked the first year in which the race was held on its now-traditional day of Saturday; all prior races had taken place anywhere from Monday through Friday. Alan-a-Dale won by a nose after going lame while he was well in front of the other horses; jockey Jimmy Winkfield held him together as the colt barely won. Inventor finished second. The Rival was third, 1⁄2 length behind Inventor. Winkfield's win in the 1902 Kentucky Derby was the last time that an African American jockey rode a winning horse in the Kentucky Derby.
The 1903 Kentucky Derby was the 29th running of the Kentucky Derby. The race took place on May 2, 1903, and offered a purse of $6,000.
The 1910 Kentucky Derby was the 36th running of the Kentucky Derby. The race took place on May 10, 1910, held at Churchill Downs racecourse in Louisville, Kentucky and was the first year in which the race times were counted in fifths of a second instead of quarters of a second in hopes of having a more accurate race duration time of the horses. The winning horse's name is Donau who was jockeyed by Frederick Herbert. Donau was awarded $4,850, second place horse received $700, and third place horse received $300.
The 1911 Kentucky Derby was the 37th running of the Kentucky Derby. The race took place on May 13, 1911. Meridian's winning time of 2:05.00 set a new Derby record.
The 1912 Kentucky Derby was the 38th running of the Kentucky Derby. The race took place on May 11, 1912.
The 1914 Kentucky Derby was the 40th running of the Kentucky Derby. The race took place on May 9, 1914. Betting favorite Old Rosebud led the entire race, winning by eight lengths. The winning time of 2.03.40 set a new Derby record, which smashed the previous year's record set by longshot Donerail. Churchill Downs president Matt Winn channeled Old Rosebud's record setting run into considerable publicity for the Derby.
The 1915 Kentucky Derby was the 41st running of the Kentucky Derby. The race took place on May 8, 1915. The winning horse, Regret, generated significant publicity for the race being the first filly to ever win the Derby. Churchill Downs president Matt Winn observed that because of Regret's win "the Derby was thus made an American institution."
The 1916 Kentucky Derby was the 42nd running of the Kentucky Derby. The race took place on May 13, 1916.
The 1917 Kentucky Derby was the 43rd running of the Kentucky Derby. The race took place on May 12, 1917. Winner Omar Khayyam, foaled in England, was the first foreign bred horse to win the Derby.
The 1918 Kentucky Derby was the 44th running of the Kentucky Derby. The race took place May 11, 1918. Exterminator went off at odds of 30–1 to the heavily favored War Cloud. Exterminator raced at the back until the field turned for home, when he launched his bid. Nearing the wire, he passed Escoba and won the Derby by a length.
The 1921 Kentucky Derby was the 47th running of the Kentucky Derby. The race took place on May 7, 1921. Behave Yourself was the upset winner of the 1921 Kentucky Derby over his stablemate, Black Servant.
The 1922 Kentucky Derby was the 48th running of the Kentucky Derby. The race took place on May 13, 1922.
Upset is notable as the only horse to have ever defeated Man o' War. Man o' War, who would go on to a career in which he won 20 of his 21 starts, faced Upset in the seventh running of the Sanford Memorial Stakes at Saratoga Race Course on August 13, 1919. Losing by a neck, Man o' War had been fractious at the starting line and got a bad start, leaving close to last. He also carried 15 pounds more than Upset. Upset finished second in the 1920 Kentucky Derby, a head behind Paul Jones, and also was second in the 1920 Preakness Stakes behind Man o' War.
The Chesapeake Stakes was an important American Thoroughbred horse race for three-year-old horses of either sex contested on dirt over a distance of a mile and one-sixteenth at Havre de Grace Racetrack in Havre de Grace, Maryland. Run from 1920 until the track closed after the 1950 edition, the race usually run in late April race was a last major prep before the Kentucky Derby. For owners who had not nominated their horse for the Derby it was a chance to test their horse's ability against some of the best three-year-olds in the country, a number of which they would undoubtedly encounter in the ensuing Preakness Stakes.
