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Charismatic, Chris Antley win 1999 Kentucky Derby (AP Photo/Patti Longmire, File)

Saturday’s Kentucky Derby features some live longshots, and one of these equine competitors could make horse racing history among the biggest upsets in the 148-year history of the event.

Since the mid-1990s, there have been a handful of longshots to turn the trick. While oddsmakers had discounted their chances, bettors backing these horses enjoyed huge paydays.

Register and bet: Use Gaming Today’s exclusive link and bonus code to claim TVG’s $200 Risk-Free Bet  

Five Biggest Kentucky Derby Upsets

2019 – Country House
Odds: 65-1
Payout: $132.40 on $2 win bet

This race ended in controversy after the apparent winner Maximum Security was disqualified for interference. Stewards deliberated for more than 20 minutes before declaring that 65-to-1 longshot Country House was the winner of the 2019 Kentucky Derby. As the 18th betting choice in the 19-horse field, Country House became the second-longest shot ever to win the Derby. Only Donerail was longer at 91-1 in 1913, and he paid out $184.90 on a $2 wager.

2009 – Mine That Bird
Odds: 50-1
Payout: $103.20 on $2 win bet

Jockey Calvin Borel was known as Calvin Bo-rail because of his propensity to make bold moves along the inside of the track. With 1/8th of a mile left in the 2009 Kentucky Derby, Borel snuck between Join In The Dance and the rail en route to a shocking victory aboard 50-to-1 Mine That Bird.

2005 – Giacomo
Odds: 50-1
Payouts: $102.60 on $2 win bet

Legendary jockey “Money” Mike Smith, who will ride Taiba in the 2022 Kentucky Derby at the age of 56 on Saturday, landed his first Derby victory on a horse that nobody expected to win. Giacomo took the lead five strides from the finish line and held off Closing Argument and Afleet Alex in a fantastic finish that shattered Kentucky Derby records for the exacta ($9,814.80), trifecta ($133,134.80), and superfecta ($1,728,507).

1999 – Charismatic
Odds: 31-1
Payout: $64.60 on $2 win bet

Hall of Fame Trainer D. Wayne Lukas won his third Kentucky Derby in five years when Charismatic pulled off an incredible upset. “’I probably never misjudged a horse early in his career as much as Charismatic,” Lukas said after the unexpected win. ”He looked like he wanted to be a fat horse who would run every two weeks. I thought, ‘If we get away with this, we ought to get out of the business.”’

1995 – Thunder Gulch
Odds: 25-1
Payout: $51 on $2 win bet

As the second-longest shot among 19 runners, Thunder Gulch was considered the least talented of Lukas’ trio of horses. Filly Serena’s Song and Timber Country were much more highly regarded. It was Serena’s Song who set a torrid pace early before Thunder Gulch crossed the finish line in 2:01.2.

Also read: Breaking Down The 2022 Kentucky Derby Field | Kentucky Derby Futures Odds From Vegas | Bonus Code For $200 Risk-Free Derby Bet At TVG

About the Author
Kris Johnson

Kris Johnson

Senior Writer
Kris Johnson is a senior writer at Gaming Today with more than 15 years of experience as a sports journalist. Johnson's work has appeared in Sports Business Daily, Sports Business Journal, NASCAR Illustrated, and other publications. He also authored a sports betting novel titled The Endgame.

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