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Kentucky Derby Betting Guide

Kentucky DerbyThe Kentucky Derby has very few rivals among American sports when it comes to tradition, history, and prestige. Contested every single year since 1875, it’s the longest-running sporting event in the United States, routinely drawing more than 150,000 people in the grandstands at historic Churchill Downs and millions of television viewers from across the globe.

It’s also among the most wagered-on events on the annual sporting calendar, and the betting handle only continues to grow. According to Kentucky Derby officials themselves, nearly $150 million was wagered on the 2018 race, representing an 8% increase from the previous year.

Want to get in on the Kentucky Derby action as well? We’re hardly surprised. The “Run for the Roses” is also commonly known as the “most exciting two minutes in sports,” delivering a unique adrenaline rush to even the most experienced and serious of gamblers.

This Kentucky Derby betting guide will tell you all that you need to know in order to wager on one of America’s greatest sporting spectacles.

When Is the Kentucky Derby?

The actual Kentucky Derby is always held on the first Saturday of May, although the annual festivities in Louisville begin long before that.

The prestigious race, which usually begins around 5:30 p.m. local time in Kentucky, marks the conclusion of the two-week Kentucky Derby Festival.

Best Betting Sites for the Kentucky Derby

The Kentucky Derby is one of the rare occasions in America where gambling isn’t just openly spoke of, but it’s literally embraced. Odds are displayed and constantly referred to throughout the NBC television broadcast, which heavily promotes TwinSpires.com as the best place to bet the race.

That’s because TwinSpires is owned and operated by Churchill Downs, the home track of the Derby itself. In reality, there are many other betting sites that you can use to bet on the Kentucky Derby, several of which may be better options for you. Any time a sporting event with the betting appeal of the Kentucky Derby takes place (other comparables are the World Cup in soccer or March Madness in college basketball), online sportsbooks tend to beef up their promotions and bonus offers in order to attract as many new customers as possible.

But while the Kentucky Derby is a great time to sign up for a new sportsbook account and take advantage of those big bonus offers, you also need to be careful of which betting site you join. A lot of sites are happy to take your money when you sign up, but they’re not quite as pleasant to deal with when you try to cash out your winnings. When selecting which betting site to play at, you need to make sure that the site has a strong history of processing withdrawals promptly and reliably and that they also honor all bonuses and promotions that they were offering.

This is where our years of experience in the online gambling industry can help you the most. We’ve gone through hundreds of betting sites and rated them by their strengths in various categories, from safety and reliability to bonus offers to customer service and more. As long as you choose from the following list of recommended betting sites for the Kentucky Derby, you’re sure to have a positive experience.

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Previous Kentucky Derby Winners

Since the Kentucky Derby is limited to three-year-old Thoroughbreds, there has never been a repeat winner of the marquee event. However, many of its champions have gone on to enjoy stellar racing careers, most notably 1973 winner Secretariat.

When Secretariat set a Kentucky Derby record by completing the 1 ¼-mile course in 1:59.40, it was a sign of great things to come. Over the next few weeks, he also raced to victory at the Preakness Stakes and Belmont Stakes, becoming just the ninth horse in history (at the time) to win the Thoroughbred Triple Crown. Ironically, Secretariat’s performance in 1973 overshadowed one of the other fastest times in Kentucky Derby history (Sham, who completed the race in 1:59.90).

Seattle Slew was another great Kentucky Derby champion, overcoming a slow start to win the 1977 Run for the Roses and improve to 7-0 all-time in his racing career. Although Seattle Slew’s time of 2:04 may not look that impressive, he still won by nearly two full lengths, suggesting that track or weather conditions might have been to blame for the slow time. Seattle Slew went on to win the Preakness and Belmont as well, making him the only horse in history to win the Triple Crown without ever having lost a race.

More recently, American Pharoah made waves in 2015 when he completed the final quarter-mile stretch in a time of 24.32 seconds, faster than Secretariat had run that leg of the race 42 years earlier. American Pharoah also captured the Preakness and Belmont that year, snapping a 38-year drought for Triple Crown champions.

Here is a list of all of the Kentucky Derby winners in history (horses with an * went on to win the Triple Crown that year):

  • 2018: Justify
  • 2017: Always Dreaming
  • 2016: Nyquist
  • 2015: American Pharoah*
  • 2014: California Chrome
  • 2013: Orb
  • 2012: I’ll Have Another
  • 2011: Animal Kingdom
  • 2010: Super Saver
  • 2009: Mine That Bird
  • 2008: Big Brown
  • 2007: Street Sense
  • 2006: Barbaro
  • 2005: Giacomo
  • 2004: Smarty Jones
  • 2003: Funny Cide
  • 2002: War Emblem
  • 2001: Monarchos
  • 2000: Fusaichi Pegasus
  • 1999: Charismatic
  • 1998: Real Quiet

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  • 1997: Silver Charm
  • 1996: Grindstone
  • 1995: Thunder Gulch
  • 1994: Go for Gin
  • 1993: Sea Hero
  • 1992: Lil E. Tee
  • 1991: Strike the Gold
  • 1990: Unbridled
  • 1989: Sunday Silence
  • 1988: Winning Colors
  • 1987: Alysheba
  • 1986: Ferdinand
  • 1985: Spend A Buck
  • 1984: Swale
  • 1983: Sunny’s Halo
  • 1982: Gato Del Sol
  • 1981: Pleasant Colony
  • 1980: Genuine Risk
  • 1979: Spectacular Bid
  • 1978: Affirmed*
  • 1977: Seattle Slew*
  • 1976: Bold Forbes
  • 1975: Foolish Pleasure
  • 1974: Cannonade
  • 1973: Secretariat*
  • 1972: Riva Ridge
  • 1971: Canonero II
  • 1970: Dust Commander
  • 1969: Majestic Prince
  • 1968: Forward Pass
  • 1967: Proud Clarion
  • 1966: Kauai King
  • 1965: Lucky Debonair
  • 1964: Northern Dancer
  • 1963: Chateaugay
  • 1962: Decidedly
  • 1961: Carry Back
  • 1960: Venetian Way
  • 1959: Tomy Lee
  • 1958: Tim Tam
  • 1957: Iron Liege
  • 1956: Needles
  • 1955: Swaps
  • 1954: Determine
  • 1953: Dark Star
  • 1952: Hill Gail
  • 1951: Count Turf
  • 1950: Middleground
  • 1949: Ponder
  • 1948: Citation*
  • 1947: Jet Pilot
  • 1946: Assault*
  • 1945: Hoop Jr.
  • 1944: Pensive
  • 1943: Count Fleet*
  • 1942: Shut Out
  • 1941: Whirlaway*
  • 1940: Gallahadion
  • 1939: Johnstown
  • 1938: Lawrin
  • 1937: War Admiral*
  • 1936: Bold Venture
  • 1935: Omaha*
  • 1934: Cavalcade
  • 1933: Brokers Tip
  • 1932: Burgoo King
  • 1931: Twenty Grand
  • 1930: Gallant Fox*
  • 1929: Clyde Van Dusen
  • 1928: Reigh Count
  • 1927: Whiskery
  • 1926: Bubbling Over
  • 1925: Flying Ebony
  • 1924: Black Gold
  • 1923: Zev
  • 1922: Morvich
  • 1921: Behave Yourself
  • 1920: Paul Jones
  • 1919: Sir Barton*
  • 1918: Exterminator
  • 1917: Omar Khayyam
  • 1916: George Smith
  • 1915: Regret
  • 1914: Old Rosebud
  • 1913: Donerail
  • 1912: Worth
  • 1911: Meridian
  • 1910: Donau
  • 1909: Wintergreen
  • 1908: Stone Street
  • 1907: Pink Star
  • 1906: Sir Huon
  • 1905: Agile
  • 1904: Elwood
  • 1903: Judge Himes
  • 1902: Alan-a-Dale
  • 1901: His Eminence
  • 1900: Lieut. Gibson
  • 1899: Manuel
  • 1898: Plaudit
  • 1897: Typhoon II
  • 1896: Ben Brush
  • 1895: Halma
  • 1894: Chant
  • 1893: Lookout
  • 1892: Azra
  • 1891: Kingman
  • 1890: Riley
  • 1889: Spokane
  • 1888: Macbeth II
  • 1887: Montrose
  • 1886: Ben Ali
  • 1885: Joe Cotton
  • 1884: Buchanan
  • 1883: Leonatus
  • 1882: Apollo
  • 1881: Hindoo
  • 1880: Fonso
  • 1879: Lord Murphy
  • 1878: Day Star
  • 1877: Baden-Baden
  • 1876: Vagrant
  • 1875: Aristides

Track Information

The Kentucky Derby is contested on a one-mile oval dirt track at Churchill Downs in Louisville, Kentucky.

Although the race itself is 1.25 miles long, the Kentucky Derby does not use a staggered start, meaning that horses in the most outside positions only have a quarter-of-a-mile stretch before they have to angle into the clubhouse turn. It also means that the horses on the most inside lanes need to make a tight turn in order to avoid running into the fence. Because of the disadvantages of being on the extreme outside or inside of the track, it should come as no surprise that Post 10 (towards the middle) has produced the most winners in Kentucky Derby history.

Rain is fairly common in Kentucky in the spring, but track officials generally do a pretty good job of maintaining a fast dirt surface for the horses to run on. As of 2014, 97 of the first 139 Kentucky Derby races had featured “fast” conditions, according to race organizers, and just 28 of the races had been contested on a “muddy,” “sloppy,” “slow,” or “heavy” track.

Kentucky Derby Records

When an event has been around for nearly 150 years, owning an all-time record carries some massive significance. Here’s a look at some of the greatest marks in the long and rich history of the Kentucky Derby.

Fastest Time

As we mentioned earlier, the legendary Secretariat is the all-time record holder when it comes to the fastest time at the Kentucky Derby, crossing the line in a time of 1:59.40 to win the 1973 race.

Only one other horse has won the Kentucky Derby in under two minutes: Monarchos, whose 1:59.97 time in 2001 was enough to win the race by an incredible 4 ¾ lengths. However, Sham (1973) technically owns the second-fastest time in Kentucky Derby history, even if his 1:59.90 time wasn’t counted in the record books, because he finished second to Secretariat.

Interestingly, while advancements in technology and training seem to make athletes bigger and faster every year, the horses at the Kentucky Derby have posted slower finishing times in recent years. Justify’s 2018 winning time of 2:04.20 was the slowest of any Kentucky Derby champion since 2010 (though it was posted in sloppy conditions), and only four horses have won the race with a time under two minutes and two seconds since 2003.

Biggest Winning Margin

The largest margin of victory in Kentucky Derby history is eight lengths, which has been accomplished by four different horses – but none since the 1940s. Old Rosebud (1914), Johnston (1939), Whirlaway (1941), and Assault (1946) each won their races by that distance, which is the equivalent of roughly 64 feet.

Only two other horses in history have won the Kentucky Derby by more than six lengths: Barbaro (2006) and Mine That Bird (2009), each of whom prevailed by 6.5.

Kentucky Derby winners who went on to win the Triple Crown typically posted comfortable margins of victory in Louisville. In fact, 2015 Triple Crown winner American Pharoah is the only one of 12 all-time Triple Crown champions who did not win the Kentucky Derby by at least 1.5 lengths (he won by one). Previous to that, Triple Crown winners averaged a 3.5-length margin of victory in the Kentucky Derby.

Biggest Field

The Kentucky Derby has grown in size over the years, expanding from a single-digit field in the 1800s to regularly featuring 20 horses in the modern era.

The largest field in Kentucky Derby history came in 1974, when 23 horses competed (10 more than the previous year). One year later, Kentucky Derby organizers decided to limit the field to 20 starters per year, which is still the largest field for any single race in the United States.

Smallest Field

Your chances of picking a Kentucky Derby winner were pretty good in 1892 and 1905, although the payouts certainly weren’t. That’s because only three horses competed in each of those races, marking the record for the smallest field in Kentucky Derby history.

The 1892 race is considered by many to be the lowest point in the history of the Kentucky Derby. At that time, the event was still less than two decades old, and it struggled to compete with the Preakness (often run the same day) and the Belmont (typically held just a few days later). Since it was harder for trainers to transport horses from the east coast to Kentucky, many of them didn’t bother, opening the door for 15-year-old Alonzo Clayton to become the youngest-ever winning jockey in Kentucky Derby history.

The small field for the 1905 Kentucky Derby was a bit more explainable, since two horses were scratched shortly before the race. The next year, the field increased to six horses, and it was up to double digits before the turn of the decade.

Winner with Highest Odds

Forget about Cal Ripken Jr.’s consecutive games streak in baseball or Wilt Chamberlain’s 100-point game in the NBA. The record in sports that is the most certain to never be broken is Donerail’s mark for being the biggest longshot to ever win the Kentucky Derby.

Not only did Donerail go off at 91:1 odds in the 1913 event (meaning that the record has already stood for more than 100 years), but he was also one of just eight horses in the field. Just imagine how outclassed Donerail must have been (or at least perceived to be) to be catching odds that high in such a small field! His victory was extra dramatic for his backers as Donerail passed the field in the final seconds to prevail by half a length.

The only longshots that even came close to Donerail’s shocking upset victory were Mine That Bird (2009) and Giacomo (2005), each of whom went off at 50:1. And while Giacomo had to work hard down the stretch to pass Afleet Alex and win by half a length, Mine That Bird’s 6 ¾ length victory was the largest margin of victory in more than 60 years.

Most Successful Trainers

Ben A. Jones is the most successful trainer in the history of the Kentucky Derby, having produced six champions of the event – including back-to-back winners in 1948 and 1949.

Jones was in charge of breeding operations at Calumet Farm in nearby Lexington throughout the 1940s, helping Calumet become one of the greatest stables in the history of Thoroughbred racing. Although Jones’ horses weren’t as successful at the Preakness and Belmont as they were at the Kentucky Derby (other than 1941 Triple Crown winner Whirlaway, only one of his horses won any other leg of the Triple Crown), he also had a hand in the development of 1948 Triple Crown champ Citation. Technically, however, Jones’ son Horace was Citation’s trainer that year.

Hot on the heels of Jones is Bob Baffert, who moved into second on the Kentucky Derby all-time trainers’ victory list with Justify’s win in 2018. Baffert’s work with Justify, who had never won a race in his life as of a few months before the Derby, has been described as the best training effort of his career. That’s saying something, considering that Baffert also produced American Pharoah. And if one more of Baffert’s horses wins a Triple Crown event, the legendary trainer will tie D. Wayne Lukas’ record of 14 combined victories at the Kentucky Derby, Preakness, and Belmont.

Most Successful Jockeys

Eddie Arcaro and Bill Hartack share the all-time Kentucky Derby record for the most victories by a jockey, each prevailing five times.

Two of Arcaro’s Kentucky Derby wins came aboard horses that he would later guide to the Triple Crown (Whirlaway in 1941, Citation in 1948), and he remains the only jockey in history to ride a pair of Triple Crown winners. Arcaro also owns the all-time record for victories in the Preakness and the Belmont, claiming each of those titles six times.

Hartack’s victories at the Kentucky Derby came in 1957, 1960, 1962, 1964, and 1969, although none of them came on an eventual Triple Crown winner. He might have surpassed Arcaro for the all-time record for Kentucky Derby wins if he hadn’t broken his leg a week before the 1958 Kentucky Derby, when the horse he was going to ride (Tam Tam) went on to victory.

Kentucky Derby History

1913 Kentucky Derby - Champion DonerailThe state of Kentucky has long been a hotbed for horses. Many of the pioneers who settled the Kentucky frontier in the late 18th century were originally from Virginia, a state known for having wealthy landowners who often imported racehorses from England. According to Slate.com, more than 92% of taxpayers in Kentucky owned at least one horse by the year 1800.

Kentucky has also been a long-time supporter of gambling on horse races, leading to many horse breeders setting up Thoroughbred nurseries in the state throughout the 1800s. So when Meriwether Lewis Clark (the grandson of William Clark, part of the famous duo Lewis and Clark) was looking to set up a major horse race that would rival England’s Epsom Derby and France’s Grand Prix de Paris Longchamps, Louisville was a perfect spot.

Clark built a racetrack on land donated by his uncles John and Henry Churchill (hence the name, Churchill Downs) and with financial support from a group of Kentucky racing enthusiasts, forming the Louisville Jockey Club. The club sponsored the first-ever Kentucky Derby in 1875, attracting 15 three-year-old Thoroughbreds in a 1.5-mile race that drew approximately 10,000 fans. In 1896, the race was shortened to 1.25 miles in an effort to make it more friendly to young Thoroughbreds early in the spring.

Although the Kentucky Derby was locally supported for the first 25 years of existence, it didn’t rise to national prominence until the early 1900s when organizers made a few significant changes. The minimum wager for the event was dropped from $5 to $2, attracting more casual gamblers, and parimutuel betting (when odds are determined by the amount of money wagered on each horse, rather than by the bookmaker) replaced the fixed odds format. Kentucky Derby officials also raised the fee to enter a horse in the race, leading to an increased purse size, and in turn, attracting higher-quality Thoroughbreds.

Another key moment in Kentucky Derby history came in 1931, when the race was permanently scheduled for the first Saturday in May. Prior to that, the race was held at various times throughout the entire month of May, often conflicting with other significant races in the country. By creating a consistent date for the Kentucky Derby, horses were now able to commit to the Preakness Stakes and Belmont Stakes as well, building the popularity of the Triple Crown.

The Kentucky Derby was first nationally televised live in 1952, when more than 10 million viewers across the country tuned in. Two years later, the prize purse for the Derby had exceeded $100,000, and by 1974, attendance for the race was as high as 160,000 fans. The race has only continued to grow in esteem and popularity since then, reaching all-time records in attendance (165,307) and wagering ($133.1 million) in 2012.


If you’ve never bet on the Kentucky Derby before, you don’t know what you’re missing! Some sporting events don’t always live up to their hype, but the “most exciting two minutes in sports” never disappoints.

Sign up at one of the best Kentucky Derby betting sites (don’t forget to check out our list of recommended sites), make a deposit, and prepare to enjoy the next Run for the Roses in a way you never have before!