2025 Kentucky Derby Free Printable Trivia Sheet: Fun Facts About Kentucky Derby History

The Kentucky Derby is the most iconic event in American horse racing, and it will be run for the 151st time in 2025. You may already know that it is a 1 ¼-mile dirt race for the best three-year-olds in the country held at Churchill Downs on the first Saturday in May. But, Kentucky Derby history is rich and full of fun facts.

You can also get ready to bet on the Kentucky Derby winner with FanDuel Racing. Explore the exciting 2025 Derby promos available on FDR. Stay updated on the Kentucky Derby Odds and Contenders as we approach the Run for the Roses!

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But first, test your Kentucky Derby knowledge with these trivia questions...

Download the free printable version here: Kentucky Derby Trivia Sheet

Kentucky Derby Trivia Questions

You can find all the questions and answers in the trivia sheet below. To download the answer key, scroll to the bottom of this page.

Question 1

Who won the first Kentucky Derby in 1875?

1. Aristides
2. Man O’ War
3. Eclipse

Answer: Aristides won the very first Kentucky Derby in 1875. He was actually entered as a rabbit for his stablemate Chesapeake, also trained by Ansel Williamson. Chesapeake was the runner who Williamson thought was better, but after starting slowly, Chesapeake didn’t fire. Aristides kept on under jockey Oliver Lewis to win by a length.

Question 2

Who started the Kentucky Derby?

1. John and Henry Churchill
2. Colonel Matt Winn
3. Meriwether Lewis Clark, Jr.

Answer: Meriwether Lewis Clark, Jr., the grandson of explorer William Clark (of Lewis and Clark fame!), began the Kentucky Derby. He had become interested in horse racing while visiting Europe. Clark built the track on land owned by his cousins John and Henry Churchill, named the track Churchill Downs, and modeled its flagship race after the Epsom Derby, a historic race in England. Colonel Matt Winn attended the first Kentucky Derby in 1875, but was only a teenager then. However, his marketing of the Kentucky Derby in the early 20th century helped make it as famous as it is today.

Question 3

Which two jockeys have won the Kentucky Derby the most times?

1. Eddie Arcaro and Bill Hartack
2. Isaac Murphy and Bill Shoemaker
3. Earle Sande and Gary Stevens

Answer: Two jockeys are tied with five Kentucky Derby wins: Eddie Arcaro and Bill Hartack. Arcaro won with Lawrin (1938), Triple Crown winner Whirlaway (1941), Hoop Jr. (1945), Triple Crown winner Citation (1948), and Hill Gail (1952). Hartack’s five winners included Iron Liege (1957), Venetian Way (1960), Decidedly (1962), Northern Dancer (1964), and Majestic Prince (1969).

Question 4

Which two trainers have won the Kentucky Derby the most times?

1. D. Wayne Lukas and Herbert “Derby Dick” Thompson
2. Bob Baffert and Ben Jones
3. “Sunny” Jim Fitzsimmons and Todd Pletcher

Answer: Ben Jones and Bob Baffert are tied for the most Kentucky Derby winners with six each. Jones’ winners include Lawrin (1938), Whirlaway (1941), Pensive (1944), Citation (1948), Ponder (1949), and Hill Gail (1952). Baffert’s six are Silver Charm (1997), Real Quiet (1998), War Emblem (2002), Triple Crown winner American Pharoah (1915), Triple Crown winner Justify (2018), and Authentic (2020). Baffert can take the record for himself alone if either Citizen Bull or Rodriguez takes the roses in 2025.

Question 5

Who is the biggest longshot to win the Kentucky Derby?

1. Country House
2. Donerail
3. Rich Strike

Answer: Though recent winners Rich Strike ($163.60) and Country House ($132.40) were colossal longshots, they still didn’t pay as much as Donerail did in 1913: he was a 91-1 shot who paid $184.90 to his few faithful backers.

Question 6

Which two horses are the heaviest favorites to win the Kentucky Derby?

1. Seattle Slew and Spectacular Bid
2. American Pharoah and Gallant Fox
3. Citation and Count Fleet

Answer: Two horses, Count Fleet (1943) and Citation (1948), were 2-5 favorites, and paid their backers just $2.80 to win. Both of them were as good as the public’s confidence suggested, as they both went on to win the Triple Crown.

Question 7

Which horse ran the fastest Kentucky Derby at its traditional 1 ¼-mile distance?

1. Monarchos
2. Stone Street
3. Secretariat

Answer: In 1973, Secretariat won the run for the roses in a dizzying 1:59.4, the fastest time in Kentucky Derby history. Two other horses have broken the two-minute barrier: Sham ran it in 1:59.8 but had the bad luck of doing so against Secretariat in 1973, meaning he had to settle for second. Monarchos, who won the Kentucky Derby in 2001, stopped the timer in 1:59.97. Stone Street holds the opposite record: his 2:15.2 in 1908 is the slowest 1 ¼-mile winning time.

Question 8

How many fillies (female horses) have won the Kentucky Derby?

1. Zero
2. Three
3. Five

Answer: Only three fillies have beaten the boys in the Kentucky Derby. Regret, the first filly to do it, was the favorite in the 1915 Kentucky Derby. It didn’t happen again until Genuine Risk rallied to win the 1980 Kentucky Derby. The most recent filly to win the Kentucky Derby was Winning Colors, who dug in to win by a neck in 1988.

Question 9

Publisher, second in the Arkansas Derby (G1), would break his maiden if he won the 2025 Kentucky Derby. But, has a horse ever broken his maiden in the Kentucky Derby?

1. Yes
2. No

Answer: Three horses have gone into the Kentucky Derby winless but gone on to win the Run for the Roses. The first was Buchanan, who won the 10th Kentucky Derby in 1884. Sir Barton won the Kentucky Derby in 1919, and went on to become the first Triple Crown winner. The last time a horse broke his maiden in the Kentucky Derby was 1933, when Brokers Tip earned his first win despite his jockey Don Meade fighting with opposing jockey Herb Fisher down the stretch!

Question 10

How many horses have had both a son and a grandson win the Kentucky Derby?

1. Zero
2. One
3. Two

Answer: There have only been two horses with both a son and a grandson to also be Kentucky Derby winners. 1928 winner Reigh Count sired 1943 Triple Crown winner Count Fleet, who in turn was the sire of the longshot winner in 1951, Count Turf. Pensive, the winner in 1944, sired 1949 winner Ponder, who went on to sire 1956 Kentucky Derby winner Needles.

Download the free printable version here: Kentucky Derby Answer Key

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