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How to Bet on the Kentucky Derby

The Kentucky Derby is an event that transcends the sport of horse racing. For some it is the “The Most Exciting Two Minutes in Sports,” and for others it serves as an excuse to throw a party to serve mint juleps and wear funny hats, as you traditionally see many women from Louisville and around the world doing in the crowd at Churchill Downs on race day.

Tennessee horse racing fans enjoy the unique challenge of handicapping the Kentucky Derby’s 20-horse field while casual horse racing fans in Tennessee are just happy to take in the spectacle of it all.

Where to bet on the Kentucky Derby

While sports betting was illegal in Tennessee and most of the United States from 1992 to 2018 due to the Professional and Amateur Sports Protection Act (PASPA), horse racing was never part of the ban by that federal law. Betting on the Kentucky Derby on websites that offer pari-mutuel betting on horse racing has been legal for decades. Tennessee does not have any physical locations to place horse racing bets at, but does allow regulated pari-mutuel horse betting sites to operate in the state.

Kentucky Derby pari-mutuel betting

Pari-mutuel betting is a form of gambling in which all of the money wagered on an event enters a pool, and the winning bettors collect money from that pool. For example, in a three-horse race in which 10 bettors bet on Horse A, 10 bettors bet on Horse B and 10 bettors bet on Horse C, the money from the bettors who bet on Horse B and Horse C will go to the bettors who bet on Horse A if Horse A wins.

Before any of these payouts happen, a cut of the pool (usually in the range of 20%-30%, depending on the track and bet type) is removed and split among the race track, operators who book horse racing bets, and other parts of the horse racing industry. The remainder of the pool goes to the winners.

Each bet type has its own pool, so the “win” pool collects money that will go to successful win bettors, the money in the “exacta” pool pays out successful exacta bettors, and so on. Unlike in sports betting where your bet locks in at the price you bet it at, pari-mutuel betting odds are not final until all of the bets on the race are in. This is why you see Kentucky Derby odds fluctuating before the race. Payouts will eventually be determined by how much money was collected in total versus how much money was bet on specific horses or outcomes.

  • Win: A bet on a horse to win the race.
  • Place: A bet on a horse to finish in first or second place.
  • Show: A bet on a horse to finish in first, second or third place.
  • Exacta: A bet on the exact order of the first place and second place horses.
  • Quinella: A bet on which two horses will finish in first and second place, in any order.
  • Trifecta: A bet on the exact order of the first, second and third place horses.
  • Superfecta: A bet on the exact order of the first, second, third and fourth place horses.

Kentucky Derby facts and records

  • First Race: 1875
  • Race Track: Churchill Downs
  • Location: Louisville, Kentucky
  • Race Distance: 1 1/4 miles (10 furlongs) since 1896
  • Most Wins by a Jockey: Eddie Arcaro and Bill Hartack, five
  • Most Wins by a Trainer: Ben A. Jones, six
  • Most Wins by an Owner: Calumet Farms, eight
  • Fastest Speed Record: Secretariat, 1:59.4, 1973
  • Largest Margin of Victory: Eight lengths, by Old Rosebud (1914), Johnstown (1939), Whirlaway (1941) and Assault (1946)

Top 10 biggest upsets in Kentucky Derby history

The 20-horse field in the Kentucky Derby has led to plenty of chaos and wild finishes over the years. These are the top 10 biggest long shots to ever cross the finish line first in the Kentucky Derby.

  1. Donerail, 1913, 91/1 — Not only did Donerail pull off the biggest upset in Triple Crown history, he did so in style by setting the new track record at 2:04 4/5. So much money had come in on the three favorites (Ten Point at 6/5, Foundation at 2/1 and Yankee Notions at 5/1) that those brave few who bet on Donerail received $184.90 on their $2 win bets.
  2. Country House, 2019, 65/1Maximum Security was a 4/1 co-favorite in the 2019 Kentucky Derby, and he was the first horse to cross the finish line. But he did so after impeding the paths of multiple horses by crossing lanes, resulting in the first disqualified winner in Kentucky Derby history. After the dust settled, second-place finisher Country House was bumped up into the winner’s circle as the second biggest long shot winner in history.
  3. Mine That Bird, 2009, 50/1 — It only took four years after Giacomo’s epic upset for another 50/1 long shot to win the Kentucky Derby. Mine That Bird was running in dead last heading into the final turn before a sensational finish on the rail that saw him blow by the rest of the field and win by 6 ¾ lengths, the biggest margin in over 60 years. He topped a $2 exacta that paid $2,074.60 and a $2 trifecta that paid $92,001.20.
  4. Giacomo, 2005, 50/1 — The 2005 Kentucky Derby field included the betting favorite Bellamy Road (2/1) and the eventual Preakness and Belmont Stakes winner Afleet Alex (4/1). Afleet Alex was in the mix late and finished in third place behind two horses no one saw coming: Giacomo at 50/1 and Closing Argument at 71/1. The historic 10-18 exacta paid $9,814.80 on a $2 bet, the 10-18-12 trifecta paid $133,134.80 and just $1 wagered on the 10-18-12-17 superfecta paid out $864,253.50.
  5. Gallahadion, 1940, 36/1Bimelech was undefeated as a 2-year-old and was one of the biggest favorites in Kentucky Derby history at 2/5 on race day. Jockey Fred Smith expended too much energy racing Bimelech wide in the Derby, allowing Gallahadion to catch him down the stretch to deliver the massive upset. Bimelech went on to win the Preakness and the Belmont in 1940.
  6. Charismatic, 1999, 31/1 — Just four years after Thunder Gulch became the first horse ever to win the Kentucky Derby from the No. 16 post in 1995, Charismatic delivered an upset win from that post in 1999. Menifee (7/1) and Cat Thief (7/1) rounded out a $2 trifecta that paid $5,866.20. Charismatic would go on to win the Preakness before falling short of the Triple Crown in the Belmont Stakes.
  7. Proud Clarion, 1967, 30/1Damascus was the horse to beat in the 1967 Kentucky Derby. He would go on to have an exceptional career with 21 wins (including the Preakness and the Belmont) and seven runner-up finishes in 32 career starts. But Damascus would settle for third place in the 1967 Kentucky Derby as it was Proud Clarion who would win the day.
  8. Exterminator, 1918, 29/1 — The Kentucky Derby field in 1918 was just eight horses, including the heavily favored War Cloud (7/5) and Escoba (4/1). But in the end Exterminator slipped through to the rail, took the lead and didn’t relinquish it to deliver the upset.
  9. Dark Star, 1953, 25/1Native Dancer, nicknamed the “Gray Ghost,” was a perfect 9-0-0 as a 2-year-old and was the clear media favorite and betting favorite leading up to the 1953 Kentucky Derby. Native Dancer raced valiantly after taking an early bump, but Dark Star took over the rail and held Native Dancer off for a narrow upset win by a head. Native Dancer would go on to win the Preakness Stakes and the Belmont Stakes.
  10. Thunder Gulch, 1995, 24/1 — Undeterred by his unfavorable starting post (No. 16) and long shot odds, Thunder Gulch ran a comfortable race right behind the leaders before eventually making a late surge to win the Kentucky Derby. Thunder Gulch proved the win was no fluke with another victory in the 1995 Belmont Stakes.

Kentucky Derby FAQ

How is the field of Kentucky Derby horses selected?

The “Road to the Kentucky Derby” was created in 2012 to make the selection process for Kentucky Derby contenders more clear than it was in previous years when it was simply based on earnings from all graded stakes races.

The Road to the Kentucky Derby is a series that includes the Kentucky Derby Prep Season and the Kentucky Derby Championship series. The number of races and small adjustments to the points structures awarded occur each year, but in general, Kentucky Derby Prep Season races award points to the top four finishers of each race in a 10-4-2-1 scale. Kentucky Derby Championship stakes races award points by a 50-20-10-5 scale, placing a greater emphasis on tougher races and current form in the months leading up to the Kentucky Derby.

The “Japan Road to the Kentucky Derby” was added in 2017 and the “European Road to the Kentucky Derby” was added in 2018, using similar points systems in stakes races in Japan and Europe to allow for the best horse out of those locations to gain entry to the Kentucky Derby.

The horse that earns the most points in the Japan road and the European road each earn one spot in the Kentucky Derby (the runners-up in these point pools receive the offer if the winner declines). The remaining 18 spots are offered in order of points collected on the Road to the Kentucky Derby until all 20 spots have been filled.

Can I cancel or change my Kentucky Derby bet after I’ve placed it?

You can change or cancel pari-mutuel bets right up until the race begins. If you bet on a horse at 6/1 to win that is now just 2/1, you can cancel your bet if you decide it is no longer a good value.

You cannot change or cancel fixed odds bets on the Kentucky Derby or other horse races with an online sportsbook once you have placed them, just like sports bets. Make sure that you want to lock your bet in before confirming it with your preferred Tennessee online sportsbook.

Has a filly ever won the Kentucky Derby?

Yes. Three fillies have won the Kentucky Derby: Regret in 1915, Genuine Risk in 1980 and Winning Colors in 1988.