Kentucky Derby Trivia

There’s no more iconic horse racing event than the Kentucky Derby. It will be run for the 152nd time in 2025. You may know already that it happens at Churchill Downs in Louisville, Kentucky. You may know already that it’s a great betting race. You may even know already about traditions like Derby hats and mint juleps. But, how much do you know about the names and stories associated with the most exciting two minutes in sports?

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Kentucky Derby Trivia Questions

Question 1:

Question: When was the first Kentucky Derby?

1. 1867
2. 1873
3. 1875

Answer: Aristides, trained by Ansel Williamson and ridden by Oliver Lewis, upset the first running of the Kentucky Derby in 1875 at Churchill Downs. The Kentucky Derby is the youngest of the three Triple Crown races: the Belmont Stakes was inaugurated in 1867, and the Preakness Stakes was first run in 1873. The Kentucky Derby has been run every year since 1875, making it the longest continually run annual sporting event in the United States. On the other hand, the other two legs of the Triple Crown have missed a few years.

Question 2:

Question: The person who started the Kentucky Derby was the grandson of which American explorer?

1. Meriwether Lewis
2. William Clark
3. Daniel Boone

Answer: The Kentucky Derby was the brainchild of Meriwether Lewis Clark, Jr., the grandson of William Clark of the Lewis and Clark expedition. (His father, son of William Clark, was named in honor of Clark’s friend and expedition partner Meriwether Lewis). Meriwether Lewis, Jr. established Churchill Downs on land owned by his cousins, John and Henry Churchill, and established a flagship race inspired by England’s Epsom Derby.

Question 3:

Question: The Kentucky Derby is traditionally the first Saturday in May, but it hasn’t been run on that date every year. During its history, it has actually been run on six different days of the week. What is the only day of the week that the Kentucky Derby hasn’t been run on?

1. Tuesday
2. Friday
3. Sunday

Answer: The Kentucky Derby has been run on every day of the week but Sunday. Saturday is the most common: the race has been on the first Saturday in May 94 times, and has been run on other Saturdays 23 times. The last time it took place on a day other than Saturday was 1910 – Donau won on Tuesday, May 10. The least common day of the week on which the Kentucky Derby was actually run is a Friday – it was only run on Friday in 1884 and 1886.

Question 4:

Question: What is the most common first letter for the name of a Kentucky Derby-winning horse?

1. B
2. C
3. S

Answer: 20 horses whose names begin with the letter S have won the Kentucky Derby as of 2025, more than any other letter. Those include 2025 winner Sovereignty as well as other top stars like Spectacular Bid, Sunday Silence, and Smarty Jones. B and C are tied for the next most winners at 13 each. There has never been a Kentucky Derby winner whose name began with Q, X, or Y.

Question 5:

Question: Which Kentucky Derby winner keyed the highest-paying exacta, trifecta, and superfecta in Kentucky Derby history?

1. Giacomo (2005)
2. Donerail (1919)
3. Rich Strike (2022)

Answer: The two highest win payouts in Kentucky Derby history were courtesy of Donerail ($184.90) and Rich Strike ($163.60), but 50-1 shot Giacomo was followed home by enough other long shots to key some dizzying exotic payouts. The $2 exacta over 71-1 shot Closing Argument paid $9,814.80. Even with 9-2 second choice Afleet Alex third, the $2 trifecta paid a dizzying $133,134.80. 29-1 shot Don’t Get Mad rounded out the superfecta, which paid a life-changing $864,253.50 for a $1 bet.

Question 6:

Question: The all-time great Man O’ War never ran in the Kentucky Derby, but two of his sons won the Kentucky Derby. Which of these winners was not by Man O’ War?

1. War Admiral
2. Manuel
3. Clyde Van Dusen

Answer: Man O’ War sired Clyde Van Dusen – named for his trainer, one Clyde Van Dusen! – as well as 1937 Triple Crown winner War Admiral. Manuel, however, was a son of Bob Miles. Manuel won the Kentucky Derby in 1899, 18 years before Man O’ War was born.

Question 7:

Question: Which of these three distances has the Kentucky Derby never been run at?

1. One mile
2. 1 ¼ miles
3. 1 ½ miles

Answer: The Kentucky Derby was run at 1 ½ miles between 1875 and 1895, the same distance as the Epsom Derby – though of course, the Kentucky Derby has always been run on a dirt track, while Epsom is run on turf. The Kentucky Derby distance was changed to 1 ¼ miles in 1896 and has been run at that distance ever since. It has never been run at a mile.

Question 8:

Question: Who is the only jockey to win the Triple Crown two times?

1. Bill Hartack
2. Ron Turcotte
3. Eddie Arcaro

Answer: Eddie Arcaro won the Triple Crown with Whirlaway in 1941 and then again with Citation in 1948. Both he and Bill Hartack won five editions of the Kentucky Derby, the most of any jockey, but Hartack never won the Triple Crown. Ron Turcotte won the Kentucky Derby twice, but Riva Ridge (1972) did not go on to win the Triple Crown. His second Kentucky Derby winner, Secretariat (1973), did.

Question 9:

Question: Who is the oldest jockey to win the Kentucky Derby?

1. Bill Shoemaker
2. John Velazquez
3. Mike Smith

Answer: Bill Shoemaker won the 1986 Kentucky Derby with Ferdinand at the age of 54 – 31 years after winning his first Kentucky Derby with Swaps. Mike Smith is the second-oldest jockey to win a Kentucky Derby, since he was 52 when he won with Justify in 2018. Smith can beat Shoemaker’s record if he wins with So Happy in 2026 – he is 60 years old. John Velazquez is already the third-oldest winner after taking the 2020 Kentucky Derby at age 48 with Authentic; he is 54 this year, but would still be about three months younger than Shoemaker was when he won if he wins with Further Ado.

Question 10:

Question: Which trainer has the most Kentucky Derby starters in history?

1. Ben Jones
2. Todd Pletcher
3. Bob Baffert

Answer: With 65 starters between 2000 and 2024, Todd Pletcher has started more horses than any trainer in the Kentucky Derby. He is expected to start a 66th in 2026 with Arkansas Derby (G1) winner Renegade. However, he does not lead in Kentucky Derby wins – he has won twice, with Super Saver in 2010 and Always Dreaming in 2017. Ben Jones and Bob Baffert are tied with the most wins, with six each. Baffert has six Kentucky Derby wins from 35 starters. Jones won his six with just 11 starters, meaning more than half his starters won the roses!

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