How to Bet on the 2020 Kentucky Derby

Kentucky Derby odds, futures and betting apps

The first running of the Kentucky Derby took place at the iconic Churchill Downs in 1875.  Since then, the best 3-year-old thoroughbreds in the world have gathered there annually on the first Saturday in May to compete in the “Run for the Roses” and a purse of $2 million.

Known as “the greatest two minutes in sports,” the Kentucky Derby is the longest-running major sporting event in the history of the US. Annually, it provides the betting community one of the most exciting horse race betting opportunities of the year.

Many potential bettors don’t take advantage because they don’t know where to begin. If you are one of these people, the purpose of this article is to explain everything you need to know to get in on the Derby Day action scheduled for Sept. 5.

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Kentucky Derby Odds

PostHorseJockeyOdds
1Finnick the FierceM. GarciaScratched
2Max PlayerR. Santana Jr.30-1
3EnforceableA. Beschizza30-1
4Storm the CourtJ. Leparoux50-1
5"Major Fed"J. Graham50-1
6King GuillermoS. CamachoScratched
7Money MovesJ. Castellano30-1
8South BendT. Gaffalione50-1
9Mr. Big NewsG. Saez50-1
10Thousand WordF. Geroux15-1
11"Necker Island"M. Mena50-1
12Sole VolanteL. Panici30-1
13Attachment RateJ. Talamo50-1
14Winning ImpressionJ. Rocco Jr.50-1
15Ny TrafficP. Lopez20-1
16Honor A. P.M. Smith5-1
17Tiz the LawM. Franco3-5
18AuthenticJ. Velazquez8-1

Kentucky Derby Futures Betting

Race day of the Kentucky Derby sees a huge number of bets placed. Many experienced bettors like to take a longer-term view on the race, betting on Kentucky Derby futures pools. There is something satisfying about spotting a potential Derby winner many months before the event – seeing it make the field of 20 and then going on to land the big prize.

Betting on KY Derby futures is simple. There is a series of 4 pools at different stages in the run up to the race. You can bet on these pools online at the leading pari-mutuel horse racing betting sites.

Kentucky Derby Futures Pool Dates

Many of the leading horse racing betting sites will publish lists of potential Derby contestants, along with odds. These are divided into pools – each with a different date. Top racing sites like TVG list these pools and offer betting options.

  • Kentucky Derby Future Wager Pool 1: November 28th – December 1st, 2019 (Closed)
  • Kentucky Derby Sire Wager: November 28th – December 1st, 2019 (Closed)
  • Kentucky Derby Future Wager Pool 2: February 7th – February 9th, 2020 (Closed)
  • Kentucky Derby Future Wager Pool 3: March 6th – March 8th, 2020 (Closed)
  • Kentucky Oaks Future Wager Pool 1: March 6th – March 8th, 2020 (Closed)
  • Kentucky Oaks / Derby Double Future Wager: March 6th – March 8th, 2020 (Closed)
  • Kentucky Derby Future Wager Pool 4: April 3rd – April 5th, 2020 (Closed)

In each of these pools you’ll find a total of 24 selections listed. The first 23 selections are the horses that the official Churchill Downs handicapper considers to be the 23 most likely to win the race. The 24th and final selection is ‘Field’, which covers every horse not on the list. You’ll see the expected payouts from each horse included with the list.

KD Future Wager Pool 1 - November 28-December 1, 2019 (CLOSED)


NumberHorseML OddsFinal OddsGross Win PoolFinal $ Odds$2 Payoff
1American Theorem50-154$4,23054.40$110.80
2Anneau d’Or20-131$7,20831.50$65
3Answer In50-164$3,58864.30$130.60
4Authentic20-150$4,52850.80$103.60
5Basin15-138$5,94138.40$78.80
6Dennis’ Moment15-112$17,98512$26
7Eight Rings15-124$9,29024.20$50.40
8Gouverneur Morris20-129$7,62929.70$61.40
9Great Power50-160$3,80860.50$123
10Green Light Go50-146$4,97146.10$94.20
11High Velocity20-140$5,67240.30$82.60
12Honor A. P.20-125$8,95225.20$52.40
13Independence Hall12-113$15,79613.80$29.60
14Maxfield15-113$16,56013.10$28.20
15Scabbard50-185$2,70585.70$173.40
16South Bend30-172$3,17872.80$147.60
17Storm the Court12-141$5,54441.30$84.60
18Structor20-124$9,03224.90$51.80
19Thousand Words15-134$6,67234.10$70.20
20Three Technique50-139$5,74339.80$81.60
21Tiz the Law20-111$18,12611.90$25.80
22Wrecking Crew50-186$2,68086.50$175
23All 3-Year-Old Fillies30-157$4,00057.60$117.20
24All Other 3YO Colts & Geldings6-51$110,4791.10$4.20

Final $ odds based on $1 payoffs

  • Win Pool Total: $284,317.00
  • Exacta Pool Total: $65,995.00
  • Total Combined: $350,312.00

KD Sire Wager Pool - November 28-December 1, 2019 (CLOSED)


#HorseML OddsFinal OddsGross Win PoolFinal $ Odds$2 Payoff
1American Pharoah812$2,02512$26
2Bernardini3037$69637$76
3Bodemeister2062$41562.80$127.60
4Candy Ride (ARG)2038$67338.30$78.60
5Constitution65$3,8795.80$13.60
6Curlin129$2,4129.90$21.80
7Declaration of War3037$68137.90$77.80
8Empire Maker2028$88428.90$59.80
9Hard Spun3031$82531.10$64.20
10Honor Code3019$1,28319.60$41.20
11Into Mischief2017$1,46217.10$36.20
12Liam’s Map3026$96426.40$54.80
13Medaglia d’Oro2021$1,17521.50$45
14More Than Ready3049$52149.80$101.60
15Pioneerof the Nile2032$79632.2$66.40
16Quality Road2030$83030.9$63.80
17Shackleford3077$33977.10$156.20
18Speightstown3073$35573.60$149.20
19Street Sense1514$1,73314.20$30.40
20Tapit1220$1,21320.80$43.60
21Tiznow1511$2,05811.80$25.60
22Uncle Mo2012$1,99312.20$26.40
23Union Rags2054$48054.20$110.40
24All Other Sires49/1$4,4294.90$11.80

Final $ odds based on $1 payoffs
Win Pool Total: $32,121.00
Exacta Pool Total: $14,961.00
Total Combined: $47,082.00

KD Future Wager Pool 2 - February 7-9, 2020 (CLOSED)


#HorseML OddsFinal OddsGross Win PoolFinal & Odds$2 Payoff
1Anneau d’Or3028$12,486.0028.00$58.00
2Authentic1515$22,484.0015.10$32.20
3Basin3039$8,884.5039.80$81.60
4Chance It3039$8,942.2539.50$81.00
5Dennis’ Moment1210$30,238.0010.90$23.80
6Enforceable3029$11,998.2529.20$60.40
7Exaulted5099$3,216.50111.70$225.40
8Gold Street3054$6,519.25054.60$111.20
9Gouverneur Morris3032$10,745.2532.70$67.40
10Honor A. P.3024$14,043.0024.80$51.60
11Independence Hall1019$17,293.0019.90$41.80
12Max Player2049$7,181.2549.50$101.00
13Maxfield1513$25,025.5013.40$28.80
14Nadal128$38,062.508.50$19.00
15Palm Springs5098$3,644.2598.50$199.00
16Premier Star5099$2,124.50169.70$341.40
17Silver State5050$6,985.7550.90$103.80
18Storm the Court3030$11,453.2530.60$63.20
19Structor3028$12,420.2528.20$58.40
20Thousand Words1516$20,247.2516.90$35.80
21Three Technique5036$9,552.2536.90$75.80
22Tiz the Law88$36,781.758.80$19.60
23Violent City5099$2,473.00145.60$293.20
24Mutuel Field (All Others)5/22$116,892.502.10$6.20

Final $ odds based on $1 payoffs

  • Win Pool Total: $439,694.00
  • Exacta Pool Total: $151,216.75
  • Total Combined: $590,910.75

KD Future Wager Pool 3 - March 6-8, 2020 (Closed)

#HorseML OddsFinal OddsGross Win PoolFinal & Odds$2 Payoff

Final $ odds based on $1 payoffs

  • Win Pool Total: TBA
  • Exacta Pool Total: TBA
  • Total Combined: TBA

Kentucky Oaks Future Wager Pool 1 - March 6-8, 2020 (Closed)

#HorseML OddsFinal OddsGross Win PoolFinal & Odds$2 Payoff

Final $ odds based on $1 payoffs

  • Win Pool Total: TBA
  • Exacta Pool Total: TBA
  • Total Combined: TBA

Kentucky Oaks Derby Double Future Wager - March 6-8, 2020 (Closed)

#HorseML OddsFinal OddsGross Win PoolFinal & Odds$2 Payoff

Final $ odds based on $1 payoffs

  • Win Pool Total: TBA
  • Exacta Pool Total: TBA
  • Total Combined: TBA

KD Future Wager Pool 4 - April 3-5, 2020 (Closed)

#HorseML OddsFinal OddsGross Win PoolFinal & Odds$2 Payoff

Final $ odds based on $1 payoffs

  • Win Pool Total: TBA
  • Exacta Pool Total: TBA
  • Total Combined: TBA

How KY Derby Futures Pools Works

In pool betting, the total stakes from all of the wagers are put into one pool (minus a small commission for running costs) and then paid out in equal parts to all of the winners.

The horses with the most money wagered will pay out a smaller amount than those with less money wagered. Final odds and/or probable payoffs will be distributed to the media and posted on horse racing betting sites following the conclusion of wagering in each respective pool. This means that you’ll know exactly what you can expect in returns if your selection wins.

How Kentucky Derby Futures Pools Change Over Time

The four pools will feature very different odds. For example, the November pool can well see the ‘field’ selection as the favorite. At this stage the overall picture regarding the race is barely taking shape. By the time pool 4 is reached in April, all of the qualifying / warm up races will have taken place. By now there will be a much clearer picture forming, and more knowledge about the line-up and the potential winners.

In addition to the race winner pool, there are two other pools you can enjoy. The first is a ‘Sire’s pool’, which lets you wager on a world class sire fathering a potential Derby winner. The other option is the Kentucky Oaks / Kentucky Derby Double, where you’ll aim to pick winners of both races – a tough task, but the rewards are there is successful.

Where to bet on the Kentucky Derby

Betting on the KY Derby has never been easier. More than half the states in the US have legal, online pari-mutuel horse wagering options available.

One absolute when selecting your Kentucky Derby wagering provider is to make sure it operates on a pari-mutuel construct, like TVG. If it does not, it won’t be linked to the massive money pool that makes betting on the Kentucky Derby great. This means the payouts will come with a cap.

For example, a doctor in Reno, NV, placed a $40 trifecta bet on the Derby at a local brick-and-mortar sportsbook in 2019. It hit at 11,500-1 odds. Combining this hit with the exacta ticket he also picked correctly, and he was set to collect a $609,000 payday.

Unfortunately, that sportsbook was not a pari-mutuel operation and had capped payouts on exotic wagers. Instead of $609,000, the bettor was only entitled to $35,000.

Let that be a lesson for us all. If you plan on wagering at your local turf club or sportsbook, do your research and avoid offshore sites.

There are 30 states that allow residents to place online horse racing wagers.

These include:

  • Alabama
  • Arkansas
  • California
  • Connecticut
  • Delaware
  • Florida
  • Illinois
  • Iowa
  • Kansas
  • Kentucky
  • Louisiana
  • Maryland
  • Massachusetts
  • Montana
  • New Hampshire
  • New York
  • North Dakota
  • Ohio
  • Oklahoma
  • Oregon
  • Pennsylvania
  • Rhode Island
  • South Dakota
  • Tennessee
  • Vermont
  • Virginia
  • Washington
  • West Virginia
  • Wisconsin
  • Wyoming

Kentucky Derby and the pari-mutuel system

Thoroughbred wagering is often conducted on a pari-mutuel platform. It is a French term meaning “to wager amongst ourselves.”

Pari-mutuel gambling is a system where individual bettors are not in competition against the track or online but, instead, are competing against the other bettors in the wagering pool.

The pari-mutuel system is a big part of what makes the Kentucky Derby such an exciting wagering opportunity. Last year, a record of $250.9 million was wagered on the Derby Day racing card, an 11% increase over 2018 (the previous record).

Pari-mutuel operators take a commission and divide the rest amongst the bettors with winning tickets. The vast pari-mutuel pool on Kentucky Derby Day creates a unique opportunity to have a chance at cashing a life-changing ticket.

Horse betting like an investor

Horse wagering is akin to an accelerated form of speculative Wall Street trading. Essentially, each horse is a commodity that is being evaluated and traded by the bettors.

A horse that is being backed is essentially a hot stock with its shares in demand. For this reason, the profit for a winning ticket on a heavily favored horse will be relatively small. On the contrary, horses that are not being bet on will generally reward their backers handsomely if they hit.

The payout odds for the horses are in constant flux as the wagers keep coming in. A wager will pay out at the final odds at the start of the race and not at the odds at the time the bet was placed.

For this reason, it is sometimes beneficial to hold off on placing a bet until close to post time, as you will have a better idea of the potential return on your investment.

Kentucky Derby bets and big payouts

There are two general categories of horse racing bets: straight and exotic. You have many choices in each category, and all have merit at one time or another. It depends on your budget, level of acceptable risk and handicapping of the race.

Straight bets

  • Win: This is a bet on a horse to win the race. In 1913, Donerail won the Kentucky Derby at 91-1 odds (paid $91 for every $1 wager). More recently, Mine That Bird made waves in 2009, claiming the roses after going off at 50-1, the same incredible odds that Giacomo paid when he won four years prior.
  • Place: This is a bet on a horse to finish first or second. It is a conservative bet that usually pays about $3-$10 on a $2 investment (but can pay less or more if the horse is a firm favorite or longshot).
  • Show: This is a bet on a horse to finish first, second or third. It is the most conservative of all racing bets and is best for horses not receiving much action (think long shots).
  • Across the Board: This is essentially three separate bets: A bet to win, a bet to place and a bet to show. If you had placed a $2 across the board bet on Mine That Bird in the 2009 Derby, the wager would have cost you $6 to make (Remember, it’s three separate bets). It would have paid you $183 ($103.20 for the win, $54 for the place and $25.80 for the show).

Exotic bets

  • Exacta: This is a bet on two horses to finish first and second, in the exact order. An exacta is the most straightforward exotic wager, and it can pay off nicely. Since 2000, the median $2 Kentucky Derby exacta payout is $306.60, with the largest being a hefty $9,814.80.
  • Quinella: This is a bet on two horses to finish first and second, in any order. This bet allows for a greater margin of error than an exacta but will not pay as much.
  • Trifecta: A bet on three horses to finish first, second and third, in the exact order. It takes the exacta bet one position further, and we’re starting to get into some significant figures now. Since the year 2000, the median $2 Kentucky Derby trifecta payout is $3,445.60, with the largest being an astounding $133,134.80. That’s enough to buy yourself a brand-new Porsche 911 and still have enough left over to get a sizable start on your kid’s college fund.
  • Superfecta: A bet on four horses to finish first, second, third and fourth, in the exact order. For those who want to shoot for the stars on Derby Day, this is it. Since the year 2000, the median $2 Kentucky Derby superfecta payout is $84,860.40, with the largest being a jaw-dropping $864,253.50. You could say goodbye to that mortgage payment.

Additional options for exotic bets

The following are examples of options available to bettors when making an exacta, trifecta or superfecta bet.

Boxing your bets

The box itself is not a bet but is an additional option when placing an exacta, trifecta or superfecta. Placing an exacta box, trifecta box or superfecta box ensures you wager all possible combinations involving your selected horses for that bet type.

For example, if you like two horses to finish at the top of a race but feel both have an even shot at winning, you could place an exacta box wager.

In this example, you are essentially making two separate exacta bets where you are flipping the order of finish of the two horses. A $2 exacta box costs $4 (two combinations), a $2 trifecta box costs $12 (six combinations) and a $2 superfecta box costs $48 (24 combinations).

As you can see, “boxing” exotic bets can quickly become expensive and may not be the most efficient option when placing trifectas and superfectas.

Wheeling your bets

Much like the box bet, a wheel is not a bet itself but is a way to place an efficient exotic bet with multiple combinations.

It is challenging to hit a superfecta with just one combination in play. But how would you feel if you could make a superfecta wheel ticket involving six different horses for less money than the superfecta box ticket that only includes four?

Let’s say you feel pretty good about picking the top three horses in the race. You could make a superfecta wheel ticket that looks like this:

  • Position 1: Horse #15
  • Position 2: Horse #16 and horse #17
  • Position 3: Horse #16, horse #17, horse #18, horse #19
  • Position 4: Horse #16, horse #17, horse #18, horse #19, horse #20

This $2 superfecta ticket costs only $36 (18 combinations). A ticket structure like this allows you to “key” horses you like at the top.

Keying horses up top allows for more possibilities in the less predictable third and fourth positions.

The Road to the Kentucky Derby

The Road to the Kentucky Derby” was established in 2012 as a series of prep races that doubles as a points system. This series determines which 3-year-old thoroughbreds qualify for the 20 post positions available at the Kentucky Derby.

The series is split into two parts: Kentucky Derby Prep Season and Kentucky Derby Championship Series. Although all these races are important, it is the second leg of the championship series that highlights most big-time Kentucky Derby contenders.

Winners of these races earn 100 points, enough to ensure them a spot in the big dance. Most second-place finishers in these races accumulate enough points to qualify as well.

Since 2017, one of the 20 available post positions has been reserved for the winner of the “Japan Road to the Kentucky Derby.”

In 2018, Churchill Downs implemented a similar construct for the “European Road to the Kentucky Derby.”

The second leg of the 2020 Road to the Kentucky Derby Championship Series consists of the following seven Grade 1 and Grade 2 stakes races:

  • Louisiana Derby
  • UAE Derby
  • Florida Derby
  • Wood Memorial
  • Blue Grass Stakes
  • Santa Anita Derby
  • Arkansas Derby

Here are some further details about these stakes races:

  • Louisiana Derby: This race was inaugurated in 1894 and is run at the Fair Grounds Race Course in New Orleans. It was run at 1 1/16 miles from 1988 to 2009 before switching to 1 1/18 in 2010. Only two Louisiana Derby winners, Black Gold in 1924 and Grindstone in 1996, have gone on to win the Kentucky Derby.
  • UAE Derby: This race is held every March at the Meydan Racecourse in Dubai as part of the Dubai World Cup night. The UAE Derby became an official race in 2000 and was added to the road to the Kentucky Derby in 2013. This contest is run at 1 3/16 miles and now boasts a $2.5 million purse. The UAE Derby has yet to produce a Kentucky Derby winner.
  • Florida Derby: This race was inaugurated in 1952 and is run at Gulfstream Park in Hallandale Beach. The Florida Derby has long been an important prep race for the Kentucky Derby and is run at 1 1/8 miles with a purse of $1 million. Fifteen winners and 24 entrants of the Florida Derby have gone on to win the Kentucky Derby, including six since the year 2000. The Florida Derby has produced more Kentucky Derby champions than any other race.
  • Wood Memorial: This race is run at 1 1/18 miles at the Aqueduct Racetrack in Queens, NY. The Wood Memorial is steeped in tradition, with 11 winners going on to take the roses between 1930 and 2000. Four winners of this race have gone on to become Triple Crown champions, more than any other Derby prep race. The Wood Memorial winner has not won the Kentucky Derby since Fusaichi Pegasus in 2000.
  • Blue Grass Stakes: This race was inaugurated in 1911 and is run at 1 1/8 miles at Keeneland Racecourse in Lexington, KY. The Blue Grass Stakes has produced 23 Kentucky Derby winners, second only to the Florida Derby (24). In an interesting twist, only 11 of those 23 finished first in the Blue Grass Stakes. Since 1996, only one Blue Grass Stakes runner, Street Sense in 2007, has gone on to win at the Twin Spires.
  • Santa Anita Derby: The jewel of Southern California was inaugurated in 1935 and is held at Santa Anita Park in Arcadia. Run at 1 1/8 miles and carrying a purse of $1 million, the Santa Anita Derby has produced 10 winners and 17 entrants that went on to win the Kentucky Derby. Three of the last eight Kentucky Derby winners were Santa Anita champions, with Justify going on to win the Triple Crown in 2018.
  • Arkansas Derby: This contest was inaugurated in 1904 and is run at 1 1/8 miles at Oaklawn Park in Hot Springs. Three winners of the Arkansas Derby have gone on to win at Churchill Downs, and two of those having done so in the past 15 years. In 2015, American Pharoah became the first Arkansas Derby winner to become a Triple Crown champion.

How to handicap the Kentucky Derby

In the US, the Kentucky Derby trailed only the Super Bowl as the highest volume handle for a single sporting event in 2019. The popularity of the Derby and the pop culture effect it embraces ensures that it is the most heavily bet horse race of the year. Also, it is the one with the most inexperienced betting pool in play.

How many times have you heard, “Our dog’s name is Max, so we’re putting our money on the number six horse Max a Million to win!”

Remember that horse betting is based on a pari-mutuel construct, which means you are competing against your fellow bettors for a share of the prize.

You don’t need to be a seasoned grinder to have a leg up on the competition on Derby Day. The most effective way to learn how to handicap the Derby is to learn how to analyze a past performances (PP) report.

Basically, PPs are report cards on the careers of each horse in the race. They contain everything you will need to make an educated wager on Derby Day and have an advantage over, e.g., the bettor who backs Max a Million.

You can purchase electronic PPs and download them for modest prices from companies like  Equibase. Single-day racecards typically go for less than $5. These providers have interactive guides on how to interpret the data contained in these reports. Several videos on YouTube will show you how to analyze them as well.

How to watch the Kentucky Derby

NBC owns the Kentucky Derby broadcast rights. You can watch Derby Day undercard races on NBC Sports Network, with coverage for the biggest races and the Derby switching to NBC late in the day.

We encourage you to use our informative article to your advantage, fund an account and responsibly enjoy the excitement that genuinely is the greatest two minutes in sports.

History of the Kentucky Derby

Kentucky Derby HistoryDubbed as ‘The Run for the Roses’ and widely known as the ‘Most Exciting Two Minutes in Sport’, the Kentucky Derby takes place annually at Churchill Downs, KT. The race is scheduled for the first Saturday in May each year.

The Kentucky Derby is the first of the three ‘Triple Crown’ events in horse racing. The Preakness Stakes and the Belmont Stakes complete this.

This page covers the Kentucky Derby in depth.  After a trip to the races formation and look at some of the lasting traditions, the winners and dramas which have unfolded over the years are covered.

How the Kentucky Derby was Established

The first ever race was run in 1875. Three years earlier Col. M. Lewis Clark had travelled to England and visited Epsom in Surrey. This is the home of English Derby which had been run since 1780. From there he travelled to Paris, where the French Jockey Club would annually run the Grand Prix de Paris at Longchamp, the largest race in France.

On returning home to Kentucky he set about forming a similar great race in the state. He did this by organizing the Louisville Jockey Club to raise money to build a facility. This track would become known as Churchill Downs.

It was on May 17th, 1875 that the very first race took place. A colt named Aristides won under jockey Oliver Lewis. This original race was run over a distance of one a half miles (replicating the Epsom Derby), before moving to the now traditional 1 mile and 2 furlongs distance in 1896.

The Kentucky Derby will always be linked with the Preakness Stakes and the Belmont Stakes, with any horses winning all three being ‘Triple Crown’ winners. This is considered the holy grail of horse racing. The first ever horse to achieve this was Sir Barton in 1919, although the phrase ‘Triple Crown’ only came into usage after ‘Gallant Fox’ was the second horse to achieve the feat in 1930.

What are the Kentucky Derby Traditions?

There are several traditions which predate the huge modern-day media coverage of the big race.

Following the call to the post, the University of Louisville Cardinal Marching Band play ‘My Old Kentucky Home’. Many in the huge crowd at Churchill Downs will be sipping on Mint Juleps, an iced drink that consists of bourbon, mint and sugar syrup.

After the race, the winning horse will be draped with a garland of 554 red roses. This originated in 1883 when New York socialite E. Berry Wall presented roses to female attendees of a ball to commemorate the legendary race. Race founder and president of the course Col. M. Lewis Clark (who was in attendance) decided to make the rose the official flower of the Kentucky Derby.

Famous Kentucky Derby Winners

Perhaps the most famous winner of the Kentucky Derby is Secretariat. This horse won the race in 1973, before famously going on to win the Triple Crown. The time of 1 minute 59.4 seconds still stands to this day as the fastest ever for the race. Sham, who finished second, also finished in under 2 minutes, and only one other horse in the history of the race has achieved this feat (Monarchos, the winner in 2001).

In total, 13 horses have won the Triple Crown – with Omaha, War Admiral, Whirlaway, Count Fleet, Assault, Citation, Seattle Slew, Affirmed, American Pharoah and most recent 2018 winner Justify, joining Secretariat, Sir Barton and Gallant Fox.

The biggest shock in the history of the Kentucky Derby came in 1913. At odds of 91-1 Donerail wasn’t considered to have a chance, but a rally off the final turn would see the horse beat favorite Ten Point by half a length. What’s more surprising is the fact that this was a new best time (the first horse to ever duck under the 2 minutes and 5 seconds mark).

Winning Jockeys and Trainers

In the history of the race, two jockeys have won it five times. Eddie Arcaro would record five wins between 1938 and 1952 (his last win coming on board Hill Gail), while Bill Hartack’s five successes came between 1957 and 1968 (his final win coming with Majestic Prince). Ben A. Jones is the top trainer in the race, with six victories coming between 1938 and 1952.

The largest margin of victory in the race is 8 lengths and this has been achieved on four occasions – Old Rosebud (1914), Johnstown (1939), Whirlaway (1941) and Assault (1946).

2019 Kentucky Derby Disqualification

Perhaps the biggest upset in the history of the Kentucky Derby came in 2019. Second favorite Maximum Security crossed the finish line in first place, ahead of outsider Country House.

However, after a lengthy 22-minute review, it was decided that Maximum Security’s swerve on the far turn had affected three other horses and he was subsequently disqualified into 17th place.

Country House therefore assumed the win and in doing so, became the second longest odds winner in the history of the race at 65.2/1. The horse would also be the first ever winner of the famous race not to cross the finish line first.

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