Get our 2024 Breeders' Cup Picks and Odds

Click here for a printable PDF version of Doc’s Sports Kentucky Derby trivia questions and answers.

If there's one thing that is obviously undeniable it's that girls dig guys who are good at trivia. The more obscure the better. If you can answer all of these Kentucky Derby trivia questions properly then you'll be a trivia god, and the girls will be all over you on Derby day. Be warned, though - these questions are very hard:

1. What filly became the first female horse to win the Kentucky Derby?

a) Winning Colors
b) Regret
c) Rags to Riches
d) Zenyatta

2. Which trainer has won the most Kentucky Derbies over his career with six?

a) D. Wayne Lukas
b) Bob Baffert
c) Ben Jones
d) Charlie Whittingham

3. It is very difficult to win the Derby wire to wire. Who was the last front runner to pull off that feat?

a) Giacomo - 2005
b) Smarty Jones - 2004
c) Funny Cide - 2003
d) War Emblem - 2002

4. There has never been a sitting President in attendance at the Derby, but one President was at the Derby just six months before he was elected to the office. Who was it?

a) John F. Kennedy
b) Franklin Roosevelt
c) Bill Clinton
d) Richard Nixon

5. We all love big payouts at the betting window. In one edition of the Derby the winner paid a stunning $184.90 for a $2 win bet. Who was that longshot winner?

a) Donerail - 1913
b) Giacomo - 2005
c) Lil E. Tee - 1992
d) Ponder - 1949

6. One of these great legends of the sport never ran in the Kentucky Derby. Who is he?

a) Secretariat
b) Man O' War
c) Curlin
d) Alydar

7. Diane Crump became the first woman ever to ride in the Kentucky Derby in 1970. There have been four other since. Who was the most recent?

a) Chantal Sutherland
b) Julie Krone
c) Rosemary Homeister Jr.
d) Donna Barton

8. The late, great Bill Shoemaker won four Kentucky Derbies, and he is the oldest winner of the race. He's almost as well known for famously choosing not to ride an eventual winner in the Derby after he had ridden him in his prep races. Who was the horse?

a) Spectacular Bid
b) Seattle Slew
c) Secretariat
d) Northern Dancer

9. Only three horses have ever run the Kentucky Derby in less than two minutes. Secretariat and Sham did it in the same race in 1973. Who is the other speedster?

a) Monarchos
b) Barbaro
c) Big Brown
d) Silver Charm

10. Winning the Kentucky Derby is not an easy or inexpensive thing to do, so it makes sense that many of the owners are very rich. Jenny Craig, the diet queen, owns Sidney's Candy, one of the entrants this year. She wouldn't agree with the business practices of Mike Pegram, the owner of 1998 winner Real Quiet. Pegram made his money as a franchisee for what company?

a) Weight Watchers
b) Dunkin Donuts
c) McDonald's
d) 7-11

Answers
1. b) Regret became the first to do it in 1915. She was followed by Genuine Risk in 1980 and Winning Colors in 1988.
2. c) Ben Jones' first win was in 1938, and his last in 1952. The last five wins were all with horses won by Calumet Farms.
3. d) Victor Espinoza rode War Emblem to the victory. He saw the horse for the first time the day of the race.
4. d) Nixon attended the 1968 Derby won by Forward Pass.
5. a) Not only was Donerail an incredibly unlikely winner, but he also set a track record in the process.
6. b) Man O' War won the Preakness and Belmont, but did not run in the Derby because his owner did not like running in Kentucky.
7. c) Rosemary Homeister Jr. was 13th aboard Supah Blitz in 2003.No woman has ever finished better than 11th.
8. d) Shoemaker opted to ride Hill Rise, a horse he had never ridden before, even though he had won the Florida Derby on Northern Dancer.
9. a) Monarchos may not have been a predictable winner, but he was certainly a fast one.
10. c) Pegram made his money owning McDonald's restaurants in Washington state before moving his business to Phoenix.

Check out Doc’s Sports homepage for the most updated Kentucky Derby Odds, post positions and field lineup, along with daily exclusive content, each day leading up to the Run for the Roses on Saturday, May 1. We also offer our expert Kentucky Derby Picks for just $20! Call us toll-free at 1-866-238-6696 for more information.