Kentucky Derby Betting Guide 2020

The Kentucky Derby is often referred to as the “most exciting two minutes in sports.”

Taking place on the first Saturday of May every year, the packed crowds at Churchill Downs get to witness tension, drama and the brilliant athleticism of both horse and jockey.

This year will see the 146th running of the race; the best thoroughbreds on the planet will aim to be in the starting field of 20 on Saturday, May 2, 2020.

This article, split into four sections, will help you gain insight into all things betting on the Kentucky Derby, as well as take a look at some of the leading contenders.

The Road to the Kentucky Derby series full of detail, while you’ll also read about the history of the race:

• How to bet the Kentucky Derby online
• Kentucky Derby betting on the Triple Crown
• How to qualify and past winners
• The history of the Kentucky Derby & FAQ

Top 3 sites for betting on the 2020 Kentucky Derby

Kentucky Derby 2019 Controversy

The Kentucky Derby is “the most exciting two minutes in sports;” however, the 2019 Derby’s drama lasted a whole lot longer. It was a full 24 minutes after post time before the final result was known.

With more than 150,000 fans packed into Churchill Downs, the excitement levels were already high. Much of the pre-race talk was about Game Winner — trained by Bob Baffert — who began the race as moneyline favorite.

Would the Triple Crown-winning trainer win the Kentucky Derby for the sixth time?

None of the audience could have predicted that they’d be witnessing one of the most enthralling and controversial races in the history of the Kentucky Derby.

The early stages of the race saw Maximum Security take up the running. After his front-running performance in the Florida Derby, the race was going as many had predicted, with a fast-opening quarter of 22.31 seconds spreading the field immediately.

With the lead, jockey Luis Saez slowed things down and controlled the pace nicely.

Coming into the final turn, it was time for Saez to make a move for home. However, in making the turn, Maximum Security moved out from the two path into the four or five path, impeding the run of War of Will.

This had a knock-on effect, as War of Will then interfered with Long Range Toddy.

Despite the trouble in running, Maximum Security would eventually pass the post first. In the meantime, 65-1 shot Country House was in ninth place heading into the final straight. He made up ground and finished in second behind Maximum Security, mostly unaffected by the action on the inside.

After the race, the jockeys of both Long Range Toddy and Country House filed an objection.

The stewards took an agonizing 22 minutes to reach a decision. In an incredible scene, they announce the decision to demote Maximum Security to 17th place, handing the win to Country House.

This was the first time in the history of the race that a winner had been disqualified for an on-track infraction.

Country House would, therefore, become the second-highest-priced winner in the history of the Kentucky Derby.

How to bet on the Kentucky Derby

In many states, you will be able to bet using specialist-pooled horse racing sites and betting apps. Examples of these include TVG, BetAmerica and Twin Spires (named after the famous twin spires of Churchill Downs itself.)

Choosing a horse betting site that is legal and has a long-standing reputation within the industry is always a good way to go. This will prove to be a better and safer choice than staking your money with any grey-market offshore site.

While both live and online legal sports betting is growing across the US, only a handful of early mover states (New Jersey, Pennsylvania and Delaware) have — or are close to having — online betting sites.

Currently, these do not include betting on horse races. This means your alternative to the horse racing betting sites is to visit your local racecourse – or even travel to Churchill Downs for the event.

Kentucky Derby betting apps

Legal horse race betting sites all are mobile device-friendly.

While the default is a browser-based version of the betting interface, you will also find apps available. You can download these onto your smartphone, giving you a stable and fast interface to place bets.

For iPhone users, the place to head to is the iTunes Store. You will find apps for TwinSpires and BetAmerica there. These apps are relatively small (58 MB) and have high ratings from their users.

If you use an Android device, then TwinSpires has you covered. You won’t find betting apps in the Google Play Store, so you must download directly from the TwinSpires website. You will need to approve this as a download from an “unknown source.”

If your favorite Kentucky Derby betting site does not offer an app, don’t worry. Websites that respond to your device’s screen size are standard these days and work perfectly for placing those bets.

Different ways to bet on the Kentucky Derby

There are several different ways in which you’ll be able to place a wager on the Kentucky Derby.

The first way is at Churchill Downs itself. The Kentucky Derby is the most attended horse race of the year. If you’re lucky enough to be at the track, then simply head to a teller and place your bet.

Many US tracks, aside from Churchill Downs, will also offer “simulcast wagering” on the day of the Kentucky Derby, so simply head down to your nearest track.

Head to one of many off-track betting (OTB) shops which are available in many US states. A simple online search should help you find your nearest OTB.

Perhaps the most straightforward option of all is to wager online, which is available from the majority of states within the US. Accounts with these sites (such as the sites mentioned above) are straightforward to set up and are secure. Stick with the regulated and legal sites, and you’ll be good to go.

Best Racing Sites for Betting on the 2020 Kentucky Derby

#1 TVG: Get $20 FREE + $100 deposit bonus

TVG is one of the longest running horse betting sites in the US. It started in 1993 (via telephone) and is now a subsidiary of global betting giant Betfair.

The company is behind the Television Games Network, which is a primary broadcaster of horse racing. You’ll find live streaming video along with the odds from 150 tracks. This site works on mobile devices via a responsive website design. It is legal in 32 states, with a range of easy deposit and withdrawal options available.

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#2 BetAmerica: A 100% welcome bonus of up to $100

 BetAmerica, founded in 2008 and is licensed by the state of Oregon, is legal to operate in 32 states.

The primary focus of this site is betting on horse racing. As well as the major US tracks, races from around the world are covered – some 200 tracks in total.

You can also bet on greyhounds, fantasy sports contests and fantasy games, which includes entertainment and political bets. BetAmerica is accessible via a responsive website or an iOS app.

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#3 TwinSpires: Bet $500 within 30 days and get a $100 free bet

This Kentucky Derby betting site is owned by Churchill Downs, where the Kentucky Derby takes place.

You’ll not only find thoroughbred racing coverage but harness racing and races from 300 tracks around the world too.

TwinSpries has apps for both iOS and Android devices, though you can also access it via your smartphone using its responsive website. Also, TwinSpires offers handicapping tools to help you make better selections.

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Types of wagers & bets

There are six main bet types on the Kentucky Derby.

• Win: This is the most straightforward wager of all. Simply bet on a horse to win the race, and if it wins, you’ll be paid out.
• Place: This time around you’re betting on your chosen horse to finish either first or second.
• Show: The show bet will see you willing your pick to finish either first, second or third.
• Exacta: The exacta bet will see you aiming to pick the first and second in order. A tough bet to win, but the rewards are there. You can “box” your exacta for an additional stake, meaning that they can finish either first or second.
• Trifecta: Trickier still is the trifecta, where you’ll be aiming to name the first, second and third place in order.
• Superfecta: The highest paying of all the wagers, here you’ll have to pick the first, second, third and fourth place.

Below is the result of the 2018 Kentucky Derby, showing the respective payouts. As you can see, if you’d bet on Justify to win, you’d receive a higher payout than if you had backed the same horse to place or show. You’ll also realize how quickly the exacta, trifecta and superfecta payouts can increase.

Kentucky Derby Payouts Based on the Type of Bet

Kentucky Derby prop bets

As well as those more standard bets you can place on the race, there are a series of prop bets on which you can wager. Many of these are based on the race itself, e.g., wagering that the winning horse’s saddlecloth number will be an even number or wagering on the exact finishing time of the race.

However, some gambling sites will also offer a number of fun bets around the race. Good examples of these are whether it will be raining when the race starts, which celebrities will be shown on screen during the rendition of My Old Kentucky Home and whether or not particular NBC experts will correctly predict the winner of the race.

So, yes, there is something for everyone when betting on the Kentucky Derby.

Past winners of the Kentucky Derby

The history of the Kentucky Derby is quite rich. Many great names have won the Kentucky Derby in the past, with perhaps the most famous of all going on to become the winner of the Preakness Stakes and the Belmont Stakes and therefore claiming the famed Triple Crown.

The first race took place in 1875, when Aristides, ridden by Oliver Lewis and trained by Ansel Williamson, would win by a couple of lengths in front of a crowd of 10,000 people – claiming a grand prize of $2,850.

In 1915, Regret won the race, and notably in the fact that she was the first filly ever to win the race and generating a significant amount of added interest in the sport.

Only three fillies have ever won the race: Regret in 1915, Genuine Risk in 1980 and Winning Colors in 1988.

The year 1919 saw Sir Barton win the Kentucky Derby before going on to become the first horse to claim the Triple Crown.

Thirteen horses have since gone on to achieve this feat, including legendary horses such as War Admiral, Seattle Slew and Affirmed. Gallant Fox and his son, Omaha, are the only father-son duo to have both claimed the Triple Crown, both trained by James “Sunny Jim” Fitzsimmons.

Baffert is the only other trainer to work with two Triple Crown winners, in 2015 and 2018 winners American Pharaoh and Justify.

Perhaps the most famous winner of the Kentucky Derby and the Triple Crown is Secretariat in 1973. Such was his legendary dominance that a feature film of the same name was released about his exploits in 2010.

List of All Kentucky Derby Winners

The road to the Kentucky Derby

The road to the Kentucky Derby features a series of races that will competitively decide which 20 horses will take their place in the starting gates on that first Saturday in May.

The series starts with 19 races named the Kentucky Derby prep series, where the first four horses will earn 10, 4, 2 and 1 points for respectively finishing first, second, third and fourth, giving racing fans an early leaderboard in the road to the Kentucky Derby itself.

The championship series sees the action ramp up with a total of 16 races.

Seven races make up the first leg of the series, with 50 points awarded to the winners (20, 10 and 5 points for second, third and fourth finishes).

A further seven races make up the second leg of the series, these making up the major events with 100 points to the winners (40, 20 and 10 points for the second, third and fourth finishes).

Two more races make up wildcard events with 20 points to the winners (8, 4 and 2 points for the second, third and fourth finishes).

Here is a rundown of all the championship series races:

The first leg of the series

The Risen Star Stakes – An American thoroughbred horse race occurs annually in February at the Fair Grounds Race Course in New Orleans and is raced over a distance of 1 1/16 miles on the dirt. It is a Grade II event open to 3-year-old horses. The Risen Star Stakes currently offers a purse of $400,000.

The Fountain of Youth Stakes – The Fountain of Youth Stakes is an American thoroughbred horse race occurs annually at Gulfstream Park in Hallandale Beach, FL, in late February over a distance of 1 1/16 miles on the dirt. It is a Grade II event open to 3-year-old horses. It currently offers a purse of $400,000.

Gotham Stakes – An American thoroughbred horse race for occurs in early March at Aqueduct Racetrack in Queens, NY, over a distance of 1 1/16 miles on the dirt. It is a Grade III event open to 3-year-old horses. Gotham Stakes currently offers a purse of $400,000.

The Tampa Bay Derby – This American thoroughbred horse race is held in mid-March at Tampa Bay Downs in Florida over a distance of 1 1/16 miles on the dirt. The Tampa Bay Derby is a Grade II event open to 3-year-old horses. It currently offers a purse of $355,000.

The San Felipe Stakes – The San Felipe Stakes is an American thoroughbred horse race held in mid-March and runs annually at Santa Anita Park in Arcadia, CA, at a distance of 1 1/16 miles on dirt. This is a Grade II event open to 3-year-old horses. It currently offers a purse of $400,000.

The Rebel Stakes – An American Grade II thoroughbred horse race is held annually in March at Oaklawn Park racetrack in Hot Springs, AR. It is raced over a distance of 1 1⁄16 miles on dirt. The Rebel Stakes is a Grade II event open to 3-year-old horses. It currently offers a purse of $1,000,000.

The Sunland Derby – An American thoroughbred horse race held in March at Sunland Park Racetrack in Sunland Park, NM. It is raced over a distance of 1.125 miles on the dirt. The Sunland Derby is a Grade III event open to 3-year-old horses. It currently offers a purse of $800,000.

2nd Leg of Series

The Louisiana Derby – The Lousiana Derby is an American thoroughbred horse race held in late March at Fair Grounds Race Course. It is raced over a distance of 1.125 miles on the dirt. A Grade III event open to 3-year-old horses. It currently offers a purse of $1,000,000.

The UAE Derby – A thoroughbred horse race held on the last Saturday in March during the Dubai World Cup Night at Meydan Racecourse in Dubai. It is raced over a distance of 1900 m (approximate 1 1/16 miles) on the dirt. The UAE is a Grade II event open to 3-year-old horses. It currently offers a purse of $2,000,000.

The Florida Derby – An American thoroughbred horse race held five weeks before the Kentucky Derby at Gulfstream Park in Hallandale Beach, Fla. It is raced over a distance of 1.125 on the dirt. The Florida Derby is a Grade I event open to 3-year-old horses. It currently offers a purse of $1,100,000.

The Wood Memorial Stakes – An American thoroughbred horse race held annually in April at Aqueduct Racetrack in South Ozone Park, Queens, NY. It is raced over a distance of 1.125 miles on the dirt. The Wood Memorial Stakes is a Grade II event open to 3-year-old horses. It currently offers a purse of $1,000,000.

The Blue Grass Stakes – An American thoroughbred horse race held annually in April at Keeneland Racecourse in Lexington, KY. It is raced over a distance of 1.125 miles on the dirt. The Blue Grass Stakes is a Grade II event open to 3-year-old horses. It currently offers a purse of $1,000,000.

The Santa Anita Derby – An American thoroughbred horse race held annually in April at Santa Anita Park in Arcadia, CA, over a distance of 1.125 miles on the dirt. This is a Grade I event open to 3-year-old horses. It currently offers a purse of $1,000,000.

The Arkansas Derby – An American thoroughbred horse race held annually in April at Oaklawn Park in Hot Springs, AK, over a distance of 1.125 miles on the dirt. The Arkansas Derby is a Grade I event open to 3-year-old horses. It currently offers a purse of $1,000,000.

Wild Card events

The Jeff Ruby Steaks – An American thoroughbred horse race held annually in late March at Turfway Park in Florence, KY, over a distance of 1.125 miles on the dirt. The Jeff Ruby Steaks is a Grade III event open to 3-year-old horses. It currently offers a purse of $200,000.

The Lexington Stakes – An American thoroughbred horse race held annually in April at Keeneland Racecourse over a distance of 1 1/16 miles on the dirt. This is a Grade III event open to 3-year-old horses. It currently offers a purse of $200,000.

As well as the “main road” to the Kentucky Derby, there are also opportunities for the leading four horses on a “European road” and one of the top four horses on the “Japan road,” too.

History of the Kentucky Derby

The idea for the Kentucky Derby came about in 1872 after Colonel Meriwether Lewis Clark Jr. (grandson of William Clark of the Lewis and Clark expedition) visited Epsom in Surrey, England, where the Derby had been run since 1780. Also, in Paris, where the Grand Prix de Paris at Longchamp, France’s greatest race at the time was run.

On returning to Kentucky, Clark organized the Louisville Jockey Club with the purpose of raising funds to build a racing facility. The facility would be called Churchill Downs, named after John and Henry Churchill, who would provide the land.

The first race was run in 1875 more than 1.5 miles (the same distance as the Epsom Derby), with Aristides the first horse ever to pass the finishing line in the Kentucky Derby. The distance of the race bumped to 1.25 miles in 1896 and remains today.

Racing fans were able to listen to the race on their radios for the first time in 1925, while the first live television coverage of the race was in 1952. The year 1970 was notable, too, as Diane Crump became the first-ever female jockey to ride in the race.

Diane Cramp was the first-ever female jockey to ride in the Kentucky Derby.

In more than 100-year history of the race, a number of traditions have been established.

The University of Louisville marching band always plays My Old Kentucky Home to kick off the race.

Mint juleps have become a staple ever since, as the legend goes, when a famous Polish actress, Helena Modjeska, ordered the drink at a pre-Derby breakfast.

The winning horse gets to wear a beautiful blanket of 564 red roses. This tradition began after Meriwether Lewis Clark used them as decorations for a post-Derby party – hence the nickname “the Race for the Roses.”

Kentucky Derby FAQ

When is the Kentucky Derby?

The Kentucky Derby always runs on the first Saturday in May; this year it will occur May 2, 2020.

The race marks the end of the Kentucky Derby Festival, which takes place over two weeks in Louisville, KY. The fest includes a balloon race, a steamboat race, a huge firework display and a parade. The Kentucky Oaks takes place the previous day on May 3.

How many horses run in the race?

In recent history, the race sets the number of runners at 20. The first race saw 15 runners, with a varied number of starters throughout the history of the race.

How much does the winner of the Kentucky Derby receive?

The overall purse for the Kentucky Derby is $3 million, with the winning connections in the race landing the first prize of $1,860,000. This compares to the sum of $2,850 awarded to the inaugural winner in 1875.

When is post time?

In 2020, the Kentucky Derby will start at 6:50 pm EST, 12 of 14 races at Churchill Downs that day. The doors open at 8 am EST at Churchill Downs, allowing fans to enjoy the all-day experience.

How much are Kentucky Derby tickets?

General admission tickets for the Kentucky Derby go on sale online in November, starting at $60. As the date for the race nears, the tickets increase in price to $70-$75, while purchasing a ticket on the day of the race itself will cost $80.

How long does the Kentucky Derby last?

Historically, the Kentucky Derby has lasted just a little more than two minutes, ever since the move to 1.25 miles in 1896, which attributes the nickname “the most exciting two minutes in sports.”

Who was the fastest horse to win the Kentucky Derby?

In the history of the Kentucky Derby, only two horses have ducked under the famed two-minute mark.

The first was Secretariat, who won the race in 1973 with a time of 1:59.04 seconds, the fastest running of the race. Monarchos romped home with a time of 1:59.97, breaking the two-minute mark in 2001.

Despite these fast-winning times, neither horse can claim the record margin of victory.

Four horses share the record-winning distance of 8 lengths:

• Old Rosebud (1914)
• Johnstown (1939)
• Whirlaway (1941)
• Assault (1946)

Which jockeys/trainers have the most wins?

Eddie Arcaro and Bill Hartack hold the joint most wins as jockeys, each crossing the line first on five occasions. Ben Jones is the most successful trainer in the history of the race with six successes.

Image credit:KElgazzar / cincinnati.com, CSpencer / miamiherald.com