A Complete Guide to the Kentucky Derby
Updated: 2025
No horse race has more of a hold on the public than the Kentucky Derby. Since the 19th century, the premier race for three-year-old Thoroughbreds has taken place at Churchill Downs in Louisville, Kentucky, the heart of horse country. And it has become nothing less than a cultural event, the one race where even casual horse racing fans come together to watch and to wager.
Many of the sport’s greatest stars, such as Secretariat, Citation, and American Pharoah, have captivated the crowds and won this prestigious race. There have been prohibitive favorites who have dominated the race, but there also have been shocking long shots who have upset the field. It is unpredictable and thrilling, and it is known as “The Fastest Two Minutes in Sports” because it seems to whoosh by in the blink of an eye.
Of course, talking about the Kentucky Derby is impossible without mentioning the betting aspects of it. Many people who don’t bet on anything all year long take out a couple bucks, head down to their local race track, and place a wager. But that can be an ordeal, especially with the big crowds who all have it in mind to do exactly the same thing.
That’s why much of the betting that takes place for the Derby occurs online. Horse racing betting sites have proliferated pretty much since the internet really started to catch on, and you can find them without looking very hard these days. Many go beyond the Kentucky Derby to include wagering opportunities on all manner of horse races, while others also include options for casino game play and other sports wagering.
Navigating these to find the highest-quality sites can sometimes be difficult, considering how many are available. That’s why we’re here to guide you through the expansive realm of Kentucky Derby betting sites. You can stick with specific sites such as KentuckyDerby.com or TwinSpires.com, which is affiliated with Churchill Downs. Or you can look for sites that offer you a little more variety.
In any case, it’s a good idea to learn a little bit about the race before you proceed. You should also understand some of the bets available to you as well as the strategies that are best utilized for the Derby. Once you have all that in hand, you can start checking out the premier betting sites for this prestigious race.
Kentucky Derby History
So how did the Kentucky Derby become the biggest race in all of America and, arguably, the entire world? It started humbly enough, with a Kentucky businessman. Meriwether Lewis Clark had visited England and witnessed the prestigious Epsom Derby. He wanted to bring such an event to his native Kentucky, which had already been established as a fertile area for horse-related businesses.
In 1875, Churchill Downs opened up for business, and the first Kentucky Derby was held on its opening day. That race, which was restricted to three-year-old horses, was captured by Aristides. The tradition was born on that day and has continued unabated since.
As for the particulars of the race, it is run on the first Saturday of May and is restricted to only the finest three-year-old horses, with a maximum field of twenty. The race is run at a distance of 1.5 miles. Other traditions include a garland of roses presented to the race winner (hence the nickname “The Run for the Roses”) and crowds decked out in their finest attire, including elaborate hats worn by the ladies.
What gave the Kentucky Derby a real boost in popularity was when it was established as the first leg of Thoroughbred racing’s Triple Crown. The Derby is followed by the Preakness Stakes and the Belmont Stakes in this prestigious trio of races for three-year-olds. Any horse that can capture all three races is truly special, considering it has occurred only 13 times in racing history.
Betting on the Kentucky Derby
Part of the lure of the Kentucky Derby is the opportunity to wager on the race. Because the fields are so big, bettors have the chance to win a lot of money for a relatively small wager if they can pick the winners. There is also a wide variety of bets available, which means that bettors aren’t limited to just trying to select the winner.
Betting in Person
You can place a wager on the Kentucky Derby in person if you happen to be at Churchill Downs on the first Saturday in May. Or you can find an off-track wagering site. These are usually located at other horse racing tracks, specific off-track wagering facilities associated with a track, or casinos or sportsbooks that accept wagers on horse racing.
If you are at one of these places, simply go up to one of the betting windows where a teller is waiting. Or you can use one of the on-site kiosks. In any case, you should know how much money you want to wager, what kind of bet you want to place, and the number of the horse (or horses) that you’re betting in the Derby.
Betting Online
You might be looking for a day out on the town with the big crowds wishing to watch the Kentucky Derby, in which case going out to bet on the race might be the choice for you. But for convenience’s sake, it’s hard to top betting online. The choices you have at your fingertips mean that you can get the best value for the money you wish to bet on the Kentucky Derby.
Your decision will likely come down to your personal preferences. Some of the details you should seek out from the horse racing betting sites at your disposal include deposit and withdrawal procedures, customer service, reputation, and potential bonuses being offered. On top of that, you should make sure that the site does indeed provide access to betting on the Kentucky Derby, as well as the most current odds.
Again, your own experience and preference will dictate your choice. But Bovada stands out as a great selection. Even though they aren’t the oldest website in the market, their bonuses are extremely competitive, and they are known for timely payouts. Still, you would be just fine dealing with any of the sites listed above; you may even have dealt with one or more of them in the past.
Betting Specifics
Because the Kentucky Derby stands above all horse races in terms of popularity in America, it means that many of the people wagering don’t have a lot of experience in that area. If that’s you, there’s no need to panic. You just need to go in with a little knowledge on the types of bets you can make, as well as some strategy, and you’ll have a great chance at finding the winner.
Bet Varieties
When you step up to the window or log in on your computer to bet on the Kentucky Derby, you’ll have excellent options regarding the types of wagers you can make. Some of these bets are easier to hit but generally pay a little less. Others require you to really be on top of the race and are extremely difficult to win, but they offer bigger payouts because of that difficulty.
For novice bettors, straight bets might be the best way to go. For example, if you just want to choose a horse to win the race, you can do so, and you will be paid at the odds listed for that horse if it wins. For example, if your Derby pick goes off at 10-1 and wins, a $2 wager will return you approximately $22. That’s ten dollars for each dollar you bet, along with your original $2 investment.
You can also bet horses to place or show. A place bet is successful if your horse comes in first or second, while a show bet is “in the money” if the horse in question finishes first, second, or third. These bets are probably the easiest to hit, but even they can be lucrative if the horse you choose doesn’t have a lot of backing from other bettors, otherwise known as a long shot.
Exotic bets are a bit more complicated and require a bit more knowledge and, quite frankly, luck to hit. What separates exotic wagers from straight bets is the fact that they include multiple horses in a race or multiple races. Prime examples of exotic bets include:
- Exacta: The first two horses in the order of finish
- Trifecta: The first three horses in the order of finish
- Superfecta: The first four horses in the order of finish
- Daily Double: The winner of two consecutive races
- Pick 3, Pick 4, etc.: The winner of three consecutive races, four consecutive races, etc.
As you might be able to surmise, exotic wagers are not easy to hit. You can make it easier by certain tactics such as boxing, which will allow you to win exactas, trifectas, and superfectas if the horses you choose come in any order. For example, if you play a 1-2 exacta box, you would win if the #1 finishes first and the #2 finishes second or if the #2 finishes first and the #1 finishes second.
Since there are up to twenty horses in a typical Kentucky Derby field, the combinations for exotics are practically limitless. As a result, the payoffs rise exponentially. An exotic wager at the Derby is the best way for you to walk away with a significant amount of scratch for a relatively small bet.
Betting Strategy
When many people bet the Kentucky Derby, they like to just pick the horses that are the best-looking or have a name that resonates with them, and that’s a fun way to go about it. But your best chance to win is if you study the past performances of the horses involved. You can find that information in a race program, which is available at the track where you bet or through a variety of online sources.
One of the things on which you can focus when it comes to betting on the Kentucky Derby is the distance of the race. At the time when they run the Derby at the beginning of May in their three-year-old season, most of the horses have never run a race that long. As a result, you should be looking for horses who have shown, in previous races, that they aren’t consistently weakening late but are actually getting stronger at the finish line.
Class is an important factor for Kentucky Derby betting. Horses who win the Derby are usually those who have been seasoned against very tough competition. Expecting a horse to come from lesser races and stand up to the rugged Kentucky Derby field is a bit of a stretch.
If you are looking for a shortcut to help you out in handicapping the field, speed figures can be extremely effective. These numbers are assigned by experts who watch every single race and try to isolate the performance of a horse when considering all of the forces working for it and against it in a particular race. Although they are far from a perfect science, speed figures can give a quick indication of the performance level of the various horses in the Derby.
Finally, many people focus on the human element of the race to help them pick winners. Owners, trainers, and jockeys all have a major impact on the success of the horses in the Derby. You can check out statistical information on these men and women not just in terms of their performances in past Kentucky Derby races, but also in terms of their recent records in general.
FAQ
Has the Kentucky Derby ever been cancelled?
Not to this point in history. Rain doesn’t stop the Derby from being run, since horses run on sloppy tracks all the time. And the May date means snow doesn’t enter the picture.
Only lightning would preclude the race from being run at its scheduled time, for the safety of horses and spectators. But even this instance would generally only require the race to be delayed until the lighting moved out of the area.
Who is the fastest Kentucky Derby winner?
The great Secretariat handled the mile-and-a-quarter distance of the Derby in 1973 in a record time of 1:59.4 (just under two minutes). In his incredible Triple Crown run, he would also go on to set speed records that year at the Preakness Stakes and the Belmont Stakes.
What jockeys and trainers have performed the best at the Kentucky Derby?
Eddie Arcaro, the legendary jockey, stands out in terms of longevity. He won the race five times and finished in the money ten times in his career. In terms of a short spurt of success, no one can match Bill Hartack, who captured five Derby victories in a twelve-year stretch (1957-1969).
On the training side of the equation, Ben Jones, who trained legendary Triple Crown winners Whirlaway and Citation in the 1940s, leads the way with six Kentucky Derby victories. But he has company in the form of Bob Baffert, the current trainer who has amassed five wins, with recent Triple Crown champions American Pharoah and Justify as the highlights.
Has a female horse ever won the Kentucky Derby?
Although the Derby is technically open to all three-year-olds, fillies rarely compete, often settling instead on the Kentucky Oaks, which is held the day before the Derby at Churchill Downs. Still, the best fillies occasionally test the waters against the boys, and three have come up successful: Regret in 1915, Genuine Risk in 1980, and Winning Colors in 1988.
Has a horse ever won the Kentucky Derby twice?
No, but only because the rules prohibit it. Only three-year-old horses can compete.
How much money is on the line for the horses at the Kentucky Derby?
Currently, the purse sits at $2 million. The lion’s share of that, a little more than 60%, goes to the connections of the winning horse. Second-place through fifth-place finishers also receive a share of that mammoth purse.
How much money is annually bet on the Kentucky Derby?
It varies from year to year. But the 2018 event should give an indication. Over $227 million was bet on the Derby alone, a new record amount at the time.
Has a long shot ever won the Kentucky Derby?
Many times, actually. The size of the field and the relative inexperience of the horses make it difficult for even the most seasoned handicappers to pinpoint which horse should be favored. As a result, many horses have won the Derby at odds greater than 10-1, which is generally the threshold for a horse to be considered a true long shot.
The biggest upset in Kentucky Derby history, according to the odds, was turned in by Donerail in 1913. He went off at odds of 91-1. That meant that those people who bet just two bucks on him to win walked away with $184.90.
