Kentucky Derby Betting

Ultimate Kentucky Derby Betting Guide. Learn how to bet on the Kentucky Derby. Here are some simple bets anyone can learn. Read on.

Kentucky Derby 147 Schedule 2021

Date & Time: Saturday, May 1, 2021. Post Time 6:57 PM ET
Place: Churchill Downs, Louisville, KY
Live Stream: NBC Live Stream
The Kentucky Derby is always the first Saturday in May.

2021 Kentucky Derby Futures Odds - Top 50 Horses
Last Updated April 30, 2021 1:34 pm
Outcometwinspires Twinspires
14. Essential Quality
15. Rock Your World
9. Hot Rod Charlie
1. Known Agenda
17. Highly Motivated
8. Medina Spirit
10. Midnight Bourbon
7. Mandaloun
19. Soup and Sandwich
18. Super Stock
6. O Besos
11. Dynamic One
16. King Fury
20. Bourbonic
5. Sainthood
13. Hidden Stash
12. Helium
4. Keepmeinmind
3. Brooklyn Strong
2. Like The King

Cached 2021-12-03 15:49:15

Recent Graded Stakes Won by Race Entries
Horse Races
Essential QualitySouthwest Stakes (2021 G3), Blue Grass Stakes (2021 G2), Belmont Stakes (2021 G1), Jim Dandy Stakes (2021 G2), Runhappy Travers Stakes (2021 G1), Claiborne Breeders Futurity (2020 G1), Breeders Cup Juvenile (2020 G1)
Rock Your WorldPasadena Stakes (2021 GL), Runhappy Santa Anita Derby (2021 G1)
Hot Rod CharlieTwinspirestakescom Louisiana Derby (2021 G2), Pennsylvania Derby (2021 G1)
Known AgendaCurlin Florida Derby (2021 G1)
Medina SpiritRobert B Lewis Stakes (2021 G3), Kentucky Derby (2021 G1), Shared Belief Stakes (2021 GL), Awesome Again Stakes (2021 G1)
Midnight BourbonLecomte Stakes (2021 G3)
MandalounRisen Star Stakes (2021 G2), Pegasus Stakes (2021 GL), Haskell Stakes (2021 G1)
Super StockArkansas Derby (2021 G1), Runhappy Ellis Park Derby (2021 GL), Zia Park Derby (2021 GL)
Dynamic OneCurlin Stakes (2021 GLR)
King FuryStonestreet Lexington Stakes (2021 G3), Street Sense Stakes (2020 GL)
BourbonicWood Memorial Stakes (2021 G2)
SainthoodPennine Ridge Stakes (2021 G3d)
HeliumTampa Bay Derby (2021 G2)
KeepmeinmindKentucky Jockey Club Stakes (2020 G2)
Brooklyn StrongRemsen Stakes (2020 G2)
Like The KingJeff Ruby Steaks (2021 G3)

2021 Kentucky Oaks Futures Odds - All Available Horses
Last Updated April 29, 2021 4:36 pm
Outcometwinspires Twinspires
Travel Column
Search Results
Crazy Beautiful
Pass The Champagne
Pauline's Pearl
Will's Secret
Competitive Speed

Cached 2021-12-03 15:49:15


  1. Best Bets
  2. 2020 Kentucky Derby Replay
  3. Best Kentucky Derby Race Call
  4. Betting Tips
  5. Kentucky Derby Longshot Winners
  6. Tables/Reference

Horse Racing Required Reading

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How to Win Kentucky Derby Betting

Profit from these Kentucky Derby bets.

1. Oaks-Derby Daily Double Bet

Pick both the Kentucky Oaks and Kentucky Derby winners. Make your picks before the Kentucky Oaks begins. Post time time is 6:12 PM the Friday before Derby Day.

The 1 1/8 mile Oaks is for 3 year old fillies. Each horse must qualify during the Oaks Prep Race period between September and April.

Racebooks determine Oaks-Derby payouts from a horse’s odds of winning its respective event.

Review the Oaks-Derby will-pays after the Oaks has concluded. Payouts include the Oaks winner paired with each Derby horse. Odds may change up until Derby post time.

Review each horse’s most recent race results. Also review Prep Race results. The Kentucky Derby and Kentucky Oaks Prep Races begin in September.

2. Win-Place-Show Bet. Also called “Across the Board”.

Pick a likely top 3 finisher. Place $2 Win, Place and Show bets on this horse. $2 x 3 bets. The entire bet costs $6 total.

Ask your track teller for $2 “Across the Board”. Or select this wager from your online race book.

Race results determine your payout. There are 4 distinct outcomes. The following lists payouts from highest to lowest.

Win-Place-Show Bet Outcomes
First Win,Place,Show None
Second Place,Show Win
Third Show Win,Place
or worse
None All

All Win-Place-Show bets lose if horse finishes fourth or worse. Also called “out of the money”.

Pick from the top 6-8 contenders. Don’t bet longshot horses unless you’re extremely confident. Avoid placing multiple Win-Place-Show bets. Consider a Trifecta or Superfecta box bet instead.

3. Kentucky Derby Quinella Box

The 20 horse Kentucky Derby field makes picking a winner difficult. Bettors must carefully manage risk to profit. Play multiple horses at once with the Quinella Box Bet.

Pick 3 or more horses to finish in the first or second position. Final order doesn’t matter.

  • Your bet wins if 2 of your selections finish first and second.
  • Bet loses if one or none of your selections finish top two.

Quinella Box bets cost $2 per combination. The following table lists costs per number of horses boxed.

Quinella Box Costs, $2 Per Combination
Horses Combinations Total

Keep Quinella Box to 6 horses or less. Larger quinella boxes are both expensive and inefficient. Consider using an Exacta Wheel bet for 6 or more horses. Key small sets of horses into each finishing position.

4. Kentucky Derby Show Bet

Your horse doesn’t have to win to turn a profit. The show bet rewards bettors for making a good-enough prediction. It manages risk like the Quinella Box. But it costs less and pays out more.

How to place a Kentucky Derby Show Bet

  1. Visit your online race book.
  2. Pick your favorite horse.
  3. Select Show Bet.
  4. Minimum bet is usually $2.

The show bet wins if your horse finishes first, second or third. Also called “in the money”. Payouts are smaller than successful win or place bets.

  • Show bets on longshots pay the most.
  • Show bets on favorites or “odds on” horses pay the least.

Consider placing Show bets on multiple horses. The 20 horse Kentucky Derby field is notoriously unpredictable. Don’t hang your hat on one selection. Diversify your bets. You’ll increase the likelihood of profiting.

2020 Kentucky Derby Replay

Best Kentucky Derby Race Call

Larry Collmus, 2011 Kentucky Derby for Animal Kingdom

Kentucky Derby Betting Tips

  1. Deposit early Kentucky Derby week. You’ll avoid last minute credit card processing glitches.
  2. Monitor Kentucky Derby Betting odds carefully. Visit your online race book’s odds page regularly. Odds will change up until post time.
  3. Shop Kentucky Derby betting odds at multiple sportsbooks.
  4. Novice bettors stick to simple +EV horse bets. Research and bet longshots carefully. Leave trifectas and superfectas to expert handicappers.

Top Kentucky Derby Longshot Winners

1. 2009 Mine That Bird 50 to 1

Jockey: Calvin Borel
2009 Kentucky Derby Winner Mine That Bird

Mine that Bird’s 2009 Kentucky Derby win was the most stunning upset in recent memory. He was the second gelding to ever win the derby, just one of nine to ever enter. It seems this unruly horse knew how to run!

A muddy start against a formidable field offered little hope. Then, as the horses broke for home, Mine that Bird surged ahead. He confidently dispatched frontrunners and late closers alike. His final time was 2:02.66, some 6+ lengths ahead of the second finisher.

Jockey Calvin Borel and trainer Bennie Woolley, Jr. were the only two people confident in this horse’s ability. Their beliefs paid off. A $2 bet paid an incredible $103.20.

Mine that Bird later finished second at the Preakness and third at the Belmont Stakes.

2. 2005 Giacomo 50 to 1

Jockey: Mike E. Smith

It was still anyone’s race down the homestretch of Kentucky Derby 131. Afleet Alex, Giacomo and Closing Argument were jockeying for the win. Ultimately Giacomo persevered in the final seventy yards defeating Closing Argument, another 50 to 1 longshot.

This improbable victory has been the only Derby win for both jockey Mike E. Smith and trainer John Shirreffs.

Giacomo’s official time was 2:02.75. He later finished third at the Preakness and seventh at the Belmont Stakes. He came back to win the 2006 San Diego Handicap, then finished fourth in the 2006 Breeders’ Cup Classic.

3. 1940 Gallahadion 36 to 1

Jockey: Carroll Bierman

Bimelech was the odds on favorite at 2 to 5 in the 1940 Kentucky Derby. Few had interest in Gallahadion, owned by the Mars candy company family.

But this 36 to 1 longshot seized the day, driving past Bimelech and Dit at the finish. He clocked a respectable 2:05.00 while time was still being marked in 1/5 seconds.

After a third place Preakness finish, Gallahadion’s luck ran out. He didn’t finish the Belmont Stakes, officially recorded as “unplaced”. Attempts to win subsequent summer races were unsuccessful.

Still, this one hit wonder makes the record books for his incredible win. Jockey Carroll Bierman and trainer Roy Waldron never won another Derby.

4. 1913 Donerail 91 to 1

Jockey: Roscoe Goose

Donerail is the biggest longshot winner of the Kentucky Derby in history. His odds were 91 to 1.

Donerail started slowly and hung with the leaders until the final stretch. There he surged to take the lead. He made his break in the final 1/16 mile leading Ten Point and Gowell to the finish.

His 2:04.8 was a record at the time. Equally impressive was the $184.90 payoff for a $2 Win bet. A Greek man named Elias Dimakos was the prescient and lucky winner.

Donerail started 62 races and won 10 before retiring in 1917. Other notable wins included the Canadian Sportsmen’s Handicap and Hamilton Cup. He appeared once again in 1918 for a turf race but dropped out before the finish.

5. 1999 Charismatic 31 to 1

Jockey: Chris Antley

Perhaps Charismatic should have been a favorite. His pedigree included Secretariat. His jockey was future hall of famer Chris Antley, who won the 1991 Derby riding Strike the Gold. Charismatic’s trainer D. Wayne Lukas had already captured 3 Derby wins. Would 1999 be his 4th?

Running to the finish, it was Cat Thief on the rail with Charismatic charging ahead. Menifee caught up on the outside, attempting to close on both horses. But Charismatic held off both as Menifee’s late surge ran out of track.

Charismatic’s 2:03.20 win cemented the legacies of both Antley and Lukas in horse racing history. He later won the Preakness.

Charismatic’s Triple Crown dreams ended painfully at the Belmont Stakes. He slowed suddenly with about 1/8 mile to go after taking the lead. Jockey Antley eased him up and dismounted, quickly grabbing Charismatic’s front-left leg. A veterinarian determined it was fractured.

Subsequent surgery returned use of the leg. But Charismatic could no longer race. He became a stud until retirement in October 2016. He died in 2017.

Kentucky Derby Betting Tables and Reference

Kentucky Derby Winners 1900 to Present

Kentucky Derby Winners
2020AuthenticJohn VelazquezBob Baffert2:00.61
2019Country HouseFlavien PratBill Mott2:03.93
2018JustifyMike E. SmithBob Baffert2:04.20
2017Always DreamingJohn VelazquezTodd Pletcher2:03.59
2016NyquistMario GutierrezDoug O'Neill2:01.31
2015American PharoahVictor EspinozaBob Baffert2:03.02
2014California ChromeVictor EspinozaArt Sherman2:03.66
2013OrbJoel RosarioClaude McGaughey III2:02.89
2012I'll Have AnotherMario GutierrezDoug O'Neill2:01.83
2011Animal KingdomJohn VelazquezH. Graham Motion2:02.04
2010Super SaverCalvin BorelTodd Pletcher2:04.45
2009Mine That BirdCalvin BorelBennie L. Woolley, Jr.2:02.66
2008Big BrownKent DesormeauxRichard E. Dutrow, Jr.2:01.82
2007Street SenseCalvin BorelCarl Nafzger2:02.17
2006BarbaroEdgar PradoMichael R. Matz2:01.36
2005GiacomoMike E. SmithJohn Shirreffs2:02.75
2004Smarty JonesStewart ElliottJohn Servis2:04.06
2003Funny CideJose A. SantosBarclay Tagg2:01.19
2002War EmblemVictor EspinozaBob Baffert2:01.13
2001MonarchosJorge F. ChavezJohn T. Ward, Jr.1:59.97
2000Fusaichi PegasusKent DesormeauxNeil Drysdale2:01.00
1999CharismaticChris AntleyD. Wayne Lukas2:03.20
1998Real QuietKent DesormeauxBob Baffert2:02.20
1997Silver CharmGary StevensBob Baffert2:02.40
1996GrindstoneJerry BaileyD. Wayne Lukas2:01.00
1995Thunder GulchGary StevensD. Wayne Lukas2:01.20
1994Go for GinChris McCarronNick Zito2:03.60
1993Sea HeroJerry BaileyMacKenzie Miller2:02.40
1992Lil E. TeePat DayLynn S. Whiting2:03.00
1991Strike the GoldChris AntleyNick Zito2:03.00
1990UnbridledCraig PerretCarl Nafzger2:02.00
1989Sunday SilencePat ValenzuelaCharlie Whittingham2:05.00
1988Winning ColorsGary StevensD. Wayne Lukas2:02.20
1987AlyshebaChris McCarronJack Van Berg2:03.40
1986FerdinandBill ShoemakerCharlie Whittingham2:02.80
1985Spend A BuckAngel Cordero, Jr.Cam Gambolati2:00.20
1984SwaleLaffit Pincay, Jr.Woody Stephens2:02.40
1983Sunny's HaloEddie DelahoussayeDavid C. Cross, Jr.2:02.20
1982Gato Del SolEddie DelahoussayeEdwin J. Gregson2:02.40
1981Pleasant ColonyJorge VelasquezJohn P. Campo2:02.00
1980Genuine RiskJacinto VasquezLeRoy Jolley2:02.00
1979Spectacular BidRonnie FranklinBud Delp2:02.40
1978AffirmedSteve CauthenLaz Barrera2:01.20
1977Seattle SlewJean CruguetWilliam H. Turner, Jr.2:02.20
1976Bold ForbesAngel Cordero, Jr.Laz Barrera2:01.60
1975Foolish PleasureJacinto VasquezLeRoy Jolley2:02.00
1974CannonadeAngel Cordero, Jr.Woody Stephens2:04.00
1973SecretariatRon TurcotteLucien Laurin1:59.40
1972Riva RidgeRon TurcotteLucien Laurin2:01.80
1971Canonero IIGustavo AvilaJuan Arias2:03.20
1970Dust CommanderMike ManganelloDon Combs2:03.40
1969Majestic PrinceBill HartackJohnny Longden2:01.80
1968Forward PassIsmael ValenzuelaHenry Forrest2:02.20
1967Proud ClarionBobby UsseryLoyd Gentry, Jr.2:00.60
1966Kauai KingDon BrumfieldHenry Forrest2:02.00
1965Lucky DebonairBill ShoemakerFrank Catrone2:01.20
1964Northern DancerBill HartackHoratio Luro2:00.00
1963ChateaugayBraulio BaezaJames P. Conway2:01.80
1962DecidedlyBill HartackHoratio Luro2:00.40
1961Carry BackJohnny SellersJack A. Price2:04.00
1960Venetian WayBill HartackVictor J. Sovinski2:02.40
1959Tomy LeeBill ShoemakerFrank E. Childs2:02.20
1958Tim TamIsmael ValenzuelaJimmy Jones2:05.00
1957Iron LiegeBill HartackJimmy Jones2:02.20
1956NeedlesDavid ErbHugh L. Fontaine2:03.40
1955SwapsBill ShoemakerMesh Tenney2:01.80
1954DetermineRaymond YorkWilliam Molter2:03.00
1953Dark StarHenry E. MorenoEddie Hayward2:02.00
1952Hill GailEddie ArcaroBen A. Jones2:01.60
1951Count TurfConn McCrearySol Rutchick2:02.60
1950MiddlegroundWilliam BolandMax Hirsch2:01.60
1949PonderSteve BrooksBen A. Jones2:04.20
1948CitationEddie ArcaroBen A. Jones2:05.40
1947Jet PilotEric GuerinTom Smith2:06.80
1946AssaultWarren MehrtensMax Hirsch2:06.60
1945Hoop Jr.Eddie ArcaroIvan H. Parke2:07.00
1944PensiveConn McCrearyBen A. Jones2:04.20
1943Count FleetJohnny LongdenDon Cameron2:04.00
1942Shut OutWayne D. WrightJohn M. Gaver, Sr.2:04.40
1941WhirlawayEddie ArcaroBen A. Jones2:01.40
1940GallahadionCarroll BiermanRoy Waldron2:05.00
1939JohnstownJames StoutJim Fitzsimmons2:03.40
1938LawrinEddie ArcaroBen A. Jones2:04.80
1937War AdmiralCharley KurtsingerGeorge Conway2:03.20
1936Bold VentureIra HanfordMax Hirsch2:03.60
1935OmahaWillie SaundersJim Fitzsimmons2:05.00
1934CavalcadeMack GarnerBob Smith2:04.00
1933Brokers TipDon MeadeHerbert J. Thompson2:06.80
1932Burgoo KingEugene JamesHerbert J. Thompson2:05.20
1931Twenty GrandCharley KurtsingerJames G. Rowe, Jr.2:01.80
1930Gallant FoxEarl SandeJim Fitzsimmons2:07.60
1929Clyde Van DusenLinus McAteeClyde Van Dusen2:10.80
1928Reigh CountChick LangBert S. Michell2:10.40
1927WhiskeryLinus McAteeFred Hopkins2:06.00
1926Bubbling OverAlbert JohnsonHerbert J. Thompson2:03.80
1925Flying EbonyEarl SandeWilliam B. Duke2:07.60
1924Black GoldJ. D. MooneyHanley Webb2:05.20
1923ZevEarl SandeDavid J. Leary2:05.40
1922MorvichAlbert JohnsonFred Burlew2:04.60
1921Behave YourselfCharles ThompsonHerbert J. Thompson2:04.20
1920Paul JonesTed RiceBilly Garth2:09.00
1919Sir BartonJohnny LoftusH. Guy Bedwell2:09.80
1918ExterminatorWillie KnappHenry McDaniel2:10.80
1917Omar KhayyamCharles BorelCharles T. Patterson2:04.60
1916George SmithJohnny LoftusHollie Hughes2:04.00
1915RegretJoe NotterJames G. Rowe, Sr.2:05.40
1914Old RosebudJohn McCabeFrank D. Weir2:03.40
1913DonerailRoscoe GooseThomas P. Hayes2:04.80
1912WorthCarroll H. ShillingFrank M. Taylor2:09.40
1911MeridianGeorge ArchibaldAlbert Ewing2:05.00
1910DonauFrederick HerbertGeorge Ham2:06.40
1909WintergreenVincent PowersCharles Mack2:08.20
1908Stone StreetArthur PickensJ. W. Hall2:15.20
1907Pink StarAndy MinderW. H. Fizer2:12.60
1906Sir HuonRoscoe TroxlerPete Coyne2:08.80
1905AgileJack MartinRobert Tucker2:10.75
1904ElwoodShorty PriorCharles E. Durnell2:08.50
1903Judge HimesHal BookerJohn P. Mayberry2:09.00
1902Alan-a-DaleJimmy WinkfieldThomas C. McDowell2:08.75
1901His EminenceJimmy WinkfieldFrank B. Van Meter2:07.75
1900Lieut. GibsonJimmy BolandCharles Hughes2:06.25

Tables and Reference

Exacta Box Costs, $2 Per Combination
Horses Combinations Total
Trifecta Box Costs, $1 Per Combination
Horses Combinations Total
Superfecta Box Costs, $1 Per Combination
Horses Combinations Total
Daily Double Wheel Costs, $1 Per Combination
Key 1 Horses Key 2 Horses Total

Kentucky Derby Required Reading