Kentucky Derby Trivia: 40 Fun Facts About the Kentucky Derby

It's time to amaze your friends with some Kentucky Derby trivia before the big race takes place on Saturday, May 4, 2024!

Know what the largest Kentucky Derby attendance was, or how many horses have run in the 150 year history of the Kentucky Derby?

Find out below with these 40 fun facts about the Kentucky Derby that will leave your friends and colleagues thinking you’re a Kentucky Derby trivia genius!

1. How old is the Kentucky Derby?

The Kentucky Derby (G1) has been run consecutively for the last 147 years.

2. When was the first Kentucky Derby?

The inaugural Kentucky Derby was run at 1 1/2 miles on dirt in 1875.

3. Who won the first Kentucky Derby?

Aristides won the first Kentucky Derby race at historic Churchill Downs Racetrack.

4. Who won the 2015 Kentucky Derby?

American Pharoah won the 141st running of the Kentucky Derby in 2:03.02, and went on to finish first in both the Preakness S. (G1) and Belmont S. (G1) to break a 37-year Triple Crown drought.

5. How many horses have run in the Kentucky Derby?

Since 1875, there have been 1,957 starters in the Kentucky Derby.

6. How many horses can run in the Kentucky Derby?

The field has been limited to 20 starters each year since 1975. This is the largest field for any single race in America.

The 1974 Derby featured the most starters (23), while the 1892 and 1905 Derby races had the fewest starters (three).

There have been 21 occasions in which the field size was comprised of 20 or more horses, and 63 occasions in which it was made up of 15 or more starters.

7. What letter has the most Kentucky Derby winners' names started with?

Horses beginning with the letter ‘S’ have won the Kentucky Derby 19 times, the last of which was Super Saver in 2010.

There have been no winners whose names begin with the letters ‘Q’, ‘X’ or ‘Y’.

8. What color horse has won the most Kentucky Derbys?

Including 2021 winner Mandaloun (who placed first after Medina Spirit’s disqualification), 56 bay horses have won the garland of roses.

Chestnut is the next most common coat color, with 48 winners, while 31 dark bay/brown horses have finished first in the Run for the Roses, and just eight gray/roan horses have earned victories. 

9. Where have the most Kentucky Derby winners been born?

Fittingly, the state where the Kentucky Derby is held is the same place where the most winners are born.

A total of 113 Derby champions have been foaled in Kentucky, while six were born in Florida, and four each came from Virginia, California, and Tennessee.

Only four winners have been born outside the United States: the British-born Tomy Lee (1959) and Omar Khayyam (1917), and Canadian-breds Sunny's Halo (1983) and Northern Dancer (1964).

Though the foals are American-born, the mares of Pensive (1944) and Cavalcade (1934) were covered in England by British stallions and shipped to the United States.

10. Who is the last foreign-bred horse to race in the Kentucky Derby?

Japanese-bred Master Fencer ran in the 2019 Kentucky Derby and finished sixth.

11. Who is the last foreign-bred horse to finish top 3 in the Kentucky Derby?

British-bred Bold Arrangement was second in the 1986 Derby.

12. Has a Kentucky Derby winner ever sired a Kentucky Derby winner?

Yes, 12 (as listed below).

  • 1895 winner Halma sired 1902 winner Alan-a-Dale
  • 1926 winner Bubbling Over sired 1932 winner Burgoo King
  • 1928 winner Reigh Count sired 1943 winner Count Fleet
  • 1930 winner Gallant Fox sired 1935 winner Omaha
  • 1936 winner Bold Venture sired 1946 winner Assault and 1950 winner Middleground
  • 1944 winner Pensive sired 1949 winner Ponder
  • 1943 winner Count Fleet sired 1951 winner Count Turf
  • 1949 winner Ponder sired 1956 winner Needles
  • 1954 winner Determine sired 1962 winner Decidedly
  • 1955 winner Swaps sired 1963 winner Chateaugay
  • 1977 winner Seattle Slew sired 1984 winner Swale
  • 1990 winner Unbridled sired 1996 winner Grindstone

13. Who is the biggest longshot in history to win the Kentucky Derby?

In 1913, 91-1 longshot Donerail was the first to cross the finish line among the small field of eight horses. Bred, owned, and trained by Thomas P. Hayes, Donerail beat favorite Ten Point by a half-length.

A $2 Win bet on Donerail paid out $184.90.

14. What is the largest margin of victory in the Kentucky Derby?

Old Rosebud (1914), Johnstown (1939), Whirlaway (1941) and Assault (1946) each won their respective Kentucky Derby races by a record margin of eight lengths. The second-largest winning margin is 6 1/2 lengths, achieved both by Barbaro (2006) and Mine That Bird (2009). 

15. What post position has won the most Kentucky Derbys?

The starting gate was first used in 1930. Since then, the winningest post has been post position 5, with 10 wins, followed by post 10, with nine wins.

The only post to never host a Derby winner is #17.

16. Has a horse ever won the Kentucky Derby without racing at two years old?

Yes, Apollo (1882) and Justify (2018).

The record of horses in the Derby without a race at 2 since 1937 is 66-1-3-5.

17. What jockey has won the most Kentucky Derby wins?

Eddie Arcaro and Bill Hartack are tied with five wins each.

Arcaro’s winning mounts include Lawrin (1938), Whirlaway (1941), Hoop Jr. (1945), Citation (1948), and Hill Gail (1952).

Hartack won with Iron Liege (1957), Venetian Way (1960), Decidedly (1962), Northern Dancer (1964), and Majestic Prince (1969).

18. What jockey has the most Kentucky Derby mounts?

In 2021, Midnight Bourbon marked Mike Smith's record-breaking 27th mount in the Run for the Roses, which broke his tie with Bill Shoemaker.

19. Have any jockeys won back-to-back Kentucky Derbys?

Yes, five (as listed below).

  • 1890-91: Isaac Murphy with Riley and Kingman
  • 1901-02: Jimmy Winkfield with His Eminence and Alan-a-Dale
  • 1972-73: Ron Turcotte with Riva Ridge and Secretariat
  • 1982-83: Eddie Delahoussaye with Gato del Sol and Sunny's Halo
  • 2009-10: Calvin Borel with Mine That Bird and Super Saver
  • 2014-15: Victor Espinoza with California Chrome and American Pharoah

20. Who is the oldest Kentucky Derby-winning jockey?

Bill Shoemaker was 54 when he won aboard Ferdinand in 1986.

21. Who is the youngest Kentucky Derby-winning jockey?

Both Alonzo Clayton (1892 on Azra) and James "Soup" Perkins (1895 on Halma) were 15 years old.

22. Has anyone won the Kentucky Derby as both a jockey and a trainer?

Yes, Johnny Longden won as a jockey on Count Fleet in 1943 and trained Majestic Prince to victory in 1969.

23. Has any jockey won the Kentucky Oaks and Kentucky Derby in the same year?

Yes, seven (as listed below).

  • 1884: Isaac Murphy with Modesty and Buchanan
  • 1933: Don Meade with Barn Swallow and Brokers Tip
  • 1950: Bill Boland with Ari's Mona and Middleground
  • 1952: Eddie Arcaro with Real Delight and Hill Gail
  • 1966: Don Brumfield with Native Street and Kauai King
  • 1993: Jerry Bailey with Dispute and Sea Hero
  • 2009: Calvin Borel with Rachel Alexandra and Mine That Bird

24. Have any female jockeys won the Kentucky Derby?

No, though six women have competed in nine runnings, with Rosie Napravnik's fifth-place finish on Mylute the best finish in 2013.

25. What trainer has the most Kentucky Derby wins?

Ben "Plain Ben" Jones and Bob Baffert are tied with six wins.

Jones’ winners are Lawrin (1938), Whirlaway (1941), Pensive (1944), Citation (1948), Ponder (1949), and Hill Gail (1952).

Baffert’s are Silver Charm (1997), Real Quiet (1998), War Emblem (2002), American Pharoah (2015), Justify (2018), and Authentic (2020).

26. What trainer has the most Kentucky Derby starts?

Two-time Derby winner Todd Pletcher has 59 starts to date, followed by D. Wayne Lukas, with 49.

27. Have any trainers won back-to-back Kentucky Derbys?

Yes, six (as listed below).

  • 1932-33: Herbert J. “Derby Dick” Thompson with Burgoo King and Brokers Tip
  • 1948-49: Ben Jones with Citation and Ponder
  • 1957-58: Jimmy Jones with Iron Liege and Tim Tam
  • 1972-73: Lucien Laurin: Riva Ridge and Secretariat
  • 1995-96: D. Wayne Lukas with Thunder Gulch and Grindstone
  • 1997-98: Bob Baffert with Silver Charm and Real Quiet

28. Who is the oldest Kentucky Derby-winning trainer?

At the age of 77, Art Sherman won his only Derby win to date with California Chrome.

29. Who is the youngest Kentucky Derby-winning trainer?

James "Jimmy" Rowe Sr. won with Hindoo at age 24 in 1881.

30. Have any father/son trainers won the Kentucky Derby?

James "Jimmy" Rowe (1881, 1915) and James Rowe Jr. (1931) were the first father-son duo to celebrate Derby glory, followed by Ben Jones (1938, 1941, 1944, 1948, 1949, 1952) and son Jimmy Jones (1957, 1958).

31. Has any trainer won the Kentucky Oaks and Kentucky Derby in the same year?

Yes. In 1933, Herbert J. “Derby Dick” Thompson was the first to do it with Brokers Tip and Barn Swallow. Ben Jones is the only other trainer to accomplish the feat and did it twice, with Wistful and Ponder (1949) and Real Delight and Hill Gail (1952).

32. Which trainer had the most Kentucky Derby starters in a single year?

Several trainers have saddled five. In 2013, Todd Pletcher raced Revolutionary (third-place finish), Charming Kitten (ninth), Overanalyze (11th), Palace Malice (12th), and Verrazano (14th). Pletcher had five starters in 2007, as well, with Circular Quay (sixth), Any Given Saturday (eighth), Sam P. (ninth), Scat Daddy (18th), and Cowtown Cat (20th).

In 2005, Nick Zito raced Bellamy Road (seventh), Andromeda's Hero (eighth), High Fly (10th), Noble Causeway (14th), and Sun King (15th).

In 1996, D. Wayne Lukas became the first trainer with five Kentucky Derby starters in a single year with Grindstone (first), Prince of Thieves (third), Editor's Note (sixth), Victory Speech (10th), and Honour and Glory (18th).

33. Have any female trainers won the Kentucky Derby?

No, but 18 female trainers have saddled a horse in the Kentucky Derby, including Vicki Oliver, the trainer of 2021 contender Hidden Stash.

The first female trainer to race a horse in the Derby was Mary Hirsch in 1937. Shelley Riley's runner-up effort with Causal Lies in 1992 is the best finish among women.

34. What is the largest Kentucky Derby attendance?

2015 marked the largest Kentucky Derby attendance, with 170,513 attendees. The following year, the Kentucky Oaks set an attendance record with 124,589 people.

35. What Kentucky Derby prep race has produced the most Kentucky Derby winners?

The Florida Derby (G1) at Gulfstream Park has had 24 runners go on to win the Derby, one more than the number from the Blue Grass S. (G2) at Keeneland. Twenty-three Derby winners also ran in the Champagne S. (G1) at Belmont, while the Hopeful S. (G1) at Saratoga and Wood Memorial (G2) at Aqueduct have each had 20 runners triumph in the Run for the Roses. 

36. What is the distance of the Kentucky Derby race?

Beginning in 1896, the Derby was shortened from 1 1/2 miles to its current distance of 1 1/4 miles, or 10 furlongs.

37. How long is the stretch run of the Kentucky Derby?

1,234.5 feet from the top of the turn to the finish line.

38. How many fillies have won the Kentucky Derby?

Three female three-year-old Thoroughbreds have won the Derby: Regret (1915), Genuine Risk (1980), and Winning Colors (1988).

39. How old do you have to be to run in the Kentucky Derby?

Three. In the Northern Hemisphere, all Thoroughbreds turn a year older on January  (vs. July 1 for horses born in the Southern Hemisphere). No matter what month a horse is actually born in, grouping together all horses born in a given year allows us to card races for age as well as distance. Some people believe there is a certain mental maturity to a horse born earlier in the year and will look to play a January-born foal over one born in April.

40. Can a horse win the Kentucky Derby more than once?

No, the race is restricted to three-year-olds on the first Saturday in May, so there is only one shot to win.