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On May 6, 2023, a three-year-old chestnut colt known as Mage became the 149th winner of the Kentucky Derby. Initially, from 1875 to 1895, the sport was a one-and-a-half-mile race between the most elite three-year-old Thoroughbreds. However, since 1896, the Kentucky Derby has been a one-and-a-quarter-mile race.

There have been a lot of spectacular winners over the years. There have also been a lot of projected winners who dropped the ball on race day. Let’s look at the biggest upset in the history of the Kentucky Derby.  

The fastest horse to ever run the Kentucky Derby 

One of the most famous horses of all time, even inspiring a 2010 movie about his life, is Secretariat. The chestnut, nicknamed Big Red, was born in the spring of 1970. He went on to win the Kentucky Derby in 1973 with a time of 1:59.4 in 1.25 miles. With this time, Secretariat remains the fastest horse to run the Kentucky Derby.

While Secretariat is the speediest to win the race, he didn’t win by the greatest margin. According to the Kentucky Derby’s official website, the greatest margin of victory is eight lengths, a record held by four different horses. These victories include Old Rosebud (1914), Johnstown (1939), Whirlaway (1941), and Assault (1946). 

Falling behind Secretariat in terms of speed, the fastest times in Kentucky Derby history were recorded by Monarchos in 2001 with a time of 1:59.97, Northern Dancer in 1964 with a time of 2:00.0, Spend A Buck in 1985 with a time of 2:00.2, and Decidedly in 1962 with a time of 2:00.4. 

The greatest upset in Kentucky Derby History 

While clear frontrunners have won the Kentucky Derby, fans have witnessed quite a few upsets over the years. In 2022, Rich Strike caused a major upset after entering the Kentucky Derby just 48 hours before the race started. Rich Strike’s entrance came due to Ethereal Road having to scratch. Winning at 80-1 odds, Rich Strike is the second-biggest longshot to win the Kentucky Derby, second only to Donerail. 

Racing at 91-1 odds, the biggest upset in Kentucky Derby history came when Donerail won the Kentucky Derby in 1913 with a time of 2:04.8. There was a record number of bets made in the 1913 race as the minimum bet was reduced to $2 for the first time. The day ended with a lot of unhappy gamblers as their bets were all thrown off by the huge upset pulled off by Donerail and jockey Roscoe Goose.

Overall, the Donerail win provided a $184.90 payoff for a $2 bet. In comparison, Rich Strike’s win paid $163.60, as reported by AP News

Only three fillies have won the Kentucky Derby 

Another interesting fact about the Kentucky Derby is that only three fillies have ever won the event. According to the Kentucky Derby Museum website, the first filly to win the Kentucky Derby was Regret in 1915. Ridden by jockey Joe Notter, the filly won the 1915 Kentucky Derby with a time of 2:05.4. Regret was born in the spring of 1912 and produced 11 foals after her Kentucky Derby win. Only one of her foals, Revenge, was a major stakes winner. 

The second filly to win the Kentucky Derby was the 1980 winner, Genuine Risk. Born in 1977, the filly won the 1980 Kentucky Derby with a time of 2:02.0. In 1982, she was bred to Secretariat. The foal would have been the first offspring in history to come from two Kentucky Derby winners. Unfortunately, the foal was stillborn in 1983.

Genuine Risk was rebred with Secretariat without success. However, the mare did give birth to two live foals in her life, Genuine Reward and Count Our Blessing. Genuine Reward went on to have a successful breeding career as a stud horse.


How Many Racehorses Have Won the Triple Crown?

The latest filly to win the Kentucky Derby was Winning Colors in 1988. The filly won the 1988 Kentucky Derby with a time of 2:02.2. As a broodmare, Winning Colors was the most successful of the three fillies to win the Kentucky Derby. She produced a total of 10 foals. Nine went on to compete, with six winning races.