2024 Kentucky Derby 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 150th time in 2024. 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.

So, saddle up and test your knowledge with our trivia sheet for the 2024 Kentucky Derby. You can download the printable sheet for free! After you've selected your answers, scroll down to check out the answers below.

Download the printable trivia sheet: Page 1 and Page 2

Trivia Sheet Answers

See if you're correct with the answers below, or download the printable answer sheet (Page 1 and Page 2). Read on to learn about Kentucky Derby history!

Question 1

Answer: (A) Aristedes

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

Question 2

Answer: (C) Meriwether Lewis Clark, Jr.

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

Answer: (A) Eddie Arcaro and Bill Hartack

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

Answer: (B) Bob Baffert and Ben Jones

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).

Question 5

Answer: (B) Donerail

Though recent winners Rich Strike and Country House 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

Answer: (C) Citation and Count Fleet

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

Answer: (C) Secretariat

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

Answer: (B) Three

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

Answer: (A) Yes

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

Answer: (C) Two

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 printable answer sheet: Page 1 and Page 2

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