How Often Do Kentucky Derby Winners Also Win Preakness Stakes?

Written By Eli Hershkovich | Published at May 14, 2024
Preakness Odds

Established at Pimlico Race Course in 1873, the Preakness Stakes was named after the first horse that won the Dinner Party Stakes in 1870. The second jewel of horse racing’s Triple Crown returns on Saturday, May 18, with Mystik Dan one-third of the way toward history if trainer Kenny McPeek gives him the opportunity. With that in mind, how often have Kentucky Derby winners also cashed in for bettors backing their Preakness Stakes odds? Let's delve into Preakness history.

Preakness history: First Two Legs Of Triple Crown

Beyond the thirteen Triple Crown winners, there have been 23 horses to emerge victorious in the Kentucky Derby and Preakness Stakes — before falling short at the Belmont Stakes. Most recently, I’ll Have Another won the 2012 Derby and the Preakness with thrilling stretch drives. Nevertheless, he was scratched from the Belmont with an injury. He was the 4-5 early favorite to win the Belmont and become the first Triple Crown winner since Affirmed in 1978.

Of course, Justify (2018) and American Pharoh (2015) have won the most recent Triple Crowns after I'll Have Another bowed out of his opportunity.

Here are the 13 horses to claim the illustrious American Triple Crown:

Below are the 23 who only delivered at the first two prestigious events:

So in the 21st century, only seven horses have won the Derby and Preakness and none since 2018. That's five consecutive years where the Derby winner has failed to find the winner's circle two weeks later.

Frequency Of Cashing In

Between the 36 horses who turned the Derby-Preakness double, including the 13 Triple Crown winners and the 26 Derby winners who hit the board at Pimlico, there have been 62 who wore the garland of roses at Churchill Downs who landed on win, place, or show tickets for the Triple Crown's middle jewel. A slew of Derby winners have also underperformed at Pimlico. In fact, 22 failed to hit the board, including Always Dreaming (eighth-place finish) in 2017.

Last year, Mage came in third, finishing just inside this elusive standing. His effort helped produce a 74.1% hit rate of Derby winners who have also placed in the money at the Preakness Stakes.

If you haven't signed up with FanDuel Racing, first-time users can place up to a $500 no-sweat bet on Preakness odds! Those already with an account on FanDuel Sportsbook are still eligible for this FanDuel Racing offer. Click "PLAY NOW" below to get started.

#
Sportsbook
Bonus
Features
Bet
1
BetMGM Up To $1500 in Bonus Bets Paid Back if your First Bet Does Not Win
  • Wide coverage of US and international sports
  • Linked to MGM Rewards loyalty program
  • Regular odds boosts and promos
Gambling problem? Call 1-800-GAMBLER or 1-800-MY-RESET (Available in the US) Call 877-8-HOPENY or text HOPENY (467369) (NY) Call 1-800-327-5050 (MA) 21+ only. Please Gamble Responsibly. Call 1-800-NEXT-STEP (AZ), 1-800-BETS-OFF (IA), 1-800-981-0023 (PR). Rewards are non-withdrawable bonus bets that expire in 7 days. In partnership with Kansas Crossing Casino and Hotel. See BetMGM.com for Terms. US promotional offers not available in DC, Mississippi, New York, Nevada, Ontario, or Puerto Rico.
2
DraftKings New Customers: Bet $5+ and get $300 in Bonus Bets if it wins!
  • Wide coverage of US and international sports
  • High-quality iOS and Android apps
  • Very fast withdrawal times
GAMBLING PROBLEM? CALL 1-800-GAMBLER or 1-800-MY-RESET, (800) 327-5050 or visit gamblinghelplinema.org (MA). Call 877-8-HOPENY/text HOPENY (467369) (NY). Please Gamble Responsibly. 888-789-7777/visit ccpg.org (CT), or visit www.mdgamblinghelp.org (MD), 1-800-981-0023 (PR). 21+ and present in most states. (18+ DC/KY/NH/PR/WY). Void in ONT/OR/NH. Eligibility restrictions apply. On behalf of Boot Hill Casino & Resort (KS). Pass-thru of per wager tax may apply in IL. 1 per new customer. Must register new account to receive reward Token. Must select Token BEFORE placing min. $5 bet to receive $200 in Bonus Bets if your bet wins. Min. -500 odds req. Token and Bonus Bets are single-use and non-withdrawable. Bet must settle by and Token expires 3/15/26. Bonus Bets expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 3/8/26 at 11:59 PM ET. Sponsored by DK.
3
Caesars Up to $250 Bonus Bet
  • Wide coverage of US and international sports
  • High-quality iOS and Android apps
  • Very fast withdrawal times
21+ New users only. Must register using eligible promo code. First bet after registration must qualify. Max. Bonus Bet: $1,000. Bonus Bet expires 14 days after receipt. Void where prohibited. See Caesars.com/promos for full terms. Gambling Problem? 1-800-GAMBLER (1-800-426-2537)
4
Hard Rock Bet Double Your Winnings on Your First 10 Bets! $50 Max Bets
  • Only sportsbook legal in Florida
  • Hot Bets feature
  • Live NFL streaming
To be eligible, the Player must be at least 21 years old, physically located in an Eligible Jurisdiction: AZ, CO, IL, IN, MI, NJ, OH, TN, or VA, and not on any exclusionary lists in any Eligible Jurisdiction. Excluded patrons are prohibited from participating in Promotions. To be eligible all personal and contact data associated to your account must be verifiable. GAMBLING PROBLEM Arizona Customers: Call 1-800-NEXT-STEP or Text NEXTSTEP to 53342. Colorado, Illinois, Michigan, New Jersey, Ohio, and Virginia Customers: Call 1-800-GAMBLER Indiana Customers: Call 1-800-9-WITH-IT Tennessee Customers: Call or text the Tennessee REDLINE: 1-800-889-9789
5
FanDuel Bet & Get up to $1,000 in Bonus Bets!
  • Offers one of the best same-game parlays
  • Highly rated mobile app
  • Impressive sports coverage
Gambling Problem? Call 1-800-GAMBLER or visit RG-help.com. Call 1-888-789-7777 or visit ccpg.org/chat (CT). Hope is here. Visit www.helpmygamblingproblem.org (MA). Play it Safe. Call 1-800-547-6133 or visit mdgamblinghelp.org (MD). Call 1-855-860-2942 or visit gamblinghelplineonline.org (WV). 21+ (18+ DC, KY, MD and restricted states for KS). An affiliation with Kansas Star Casino. First online real money wager only. $5 free deposit credited. Bonus credited upon wager of $5 or more within 72 days after receipt. Restrictions apply. See terms at sportsbook.fanduel.com.
6
Fanatics Bet $50, Get $300 in FanCash
  • Unique FanCash loyalty program
  • Variety of bonuses and ongoing promos
  • Fast, reliable app with live betting and streaming
Must be 21+. GAMBLING PROBLEM? CALL 1-800-GAMBLER or 1-800-522-4700, Home (MD), (800)-327-5050 or MA Gambling Helpline (MA), Call (877)8-HOPENY or text HOPENY (467369) (NY), or Call 1-800-NEXT-STEP or text NEXTSTEP to 53342 (AZ), (888) 789-7777 or CONNECTICUT COUNCIL – ON PROBLEM GAMBLING (CT), or 1-800-9-WITH-IT (IN), If gambling is more than a game, free help is available . . . - NCDHHS Problem Gambling (NC). New customers in AZ, CO, CT, DC, IA, IL, IN, KS, KY, LA, MA, MD, MI, MO, NC, NJ, NY, OH, PA, TN, VA, VT, WV, or WY. Must opt-in and wager $10+ cash on any market with odds of -500 or longer to receive $100 in FanCash each day for your first 3 days (issued when qualifying wager settles). Your 3 days begin the day you establish your account. FanCash rewards expire at 11:59 p.m. ET 7 days from issuance. Terms, including FanCash terms, apply - see Fanatics Sportsbook app.

Discover more on how to bet on the Preakness Stakes!

*Some information courtesy of Pimlico Racing News and press releases