Kentucky Derby Betting: 5 Biggest Longshots To Ever Win

Written By Brett Gibbons on May 5, 2023
kentucky derby longshots

One of the greatest moments in all of sports is watching a longshot race horse cross the finish line first in the Kentucky Derby. Just last year, Rich Strike, who sat 80-1 at the gate, pulled off one of the biggest upsets in Derby history. Seemingly the entire country watched on bated breath as Rich Strike closed the gap and finish a nose ahead of the competition. But Rich Strike was only the second largest upset in Kentucky Derby history.

Below, we’ll look at the five biggest longshots to ever win the Kentucky Derby.

Get a $20 No Sweat Preakness Bet at FanDuel Racing
Preakness BET
Bet on the Preakness Stakes
Up to $20 Back if Your Bet Doesn't Win
Get Boosted Odds & the Best Promotions
Easy Deposits, Fast Withdrawals
To Claim: Click Play Now

5 Biggest Longshots To Win The Kentucky Derby

Historic odds below courtesy of Churchill Downs.

5. Giacomo, 50-1 (2005)

Ridden by Hall of Fame jockey Mike E. Smith, Giacomo came up from 17th place to start, closing a massive gap in a blazing half-mile pace (:45.2). Smith notched his first Derby victory in the race. Like many Derby longshot winners, Giacomo would drop races in both the Preakness (third) and Belmont (seventh). But his victory in 2005 stands as one of the legendary performances and, at the time, was the second-largest upset ever.

4. Mine That Bird, 50-1 (2009)

On a sloppy track, Mine That Bird came from a distant last to a distant first, finishing nearly 16 lengths ahead of the pack. That victory tied the second-longest ever upset at the time and was the largest margin of victory at the Kentucky Derby in over 60 years. He rode the rail from last to first coming off the second turn and shocked the horse racing world.

3. Country House, 65-1 (2019)

2019 featured one of the most difficult Derby tracks in recent memory. He started out of Gate 20 and settled in behind the bulk of the pack early. Maximum Security crossed the line first, but was later disqualified due to veering into two other horses. Jockey Luis Saez was able to straighten him out, but officials declared Maximum Security DQ’d. It’s a controversial finish, but Country House bettors ultimately got the payout.

  • Follow TheLines on Twitter for complete Kentucky Derby coverage.

2. Rich Strike, 80-1 (2022)

At 8:00 a.m. on Friday, May 6, 2022, Rich Strike was not in the Kentucky Derby field. By 7:00 p.m. on Saturday, May 7, he had won it. A last-second scratch in the field vaulted the 21st horse – Rich Strike – into the field, who closed at 80-1 improbable odds. Not only did Rich Strike beat out one of the deepest Derby field in recent memory, jockey Sonny Leon expertly weaved him through the field, rather than taking an inside or outside lane. He won by a nose, finishing with one of the fastest final stretches ever.

1. Donerail, 91-1 (1913)

Despite a slew of longshots to win the Kentucky Derby in the 2000s, Donerail’s upset remains, and may remain, unbeaten. Coincidentally, Churchill Downs had just undergone massive renovation for the 1913 run and betting limits were lowered to $2. Donerail was housed three miles from the track, since this year’s field was “overcrowded.” Given this was in 1913, Donerail walked to the race track. He ended the day by setting a track record at the time, 2:04.8.

TheLines’ Free Kentucky Derby Challenge: Hit A Trifecta To Win $100 Amazon Gift Card

Top Sportsbook Promos In Your State

UP TO $1,250 BONUS
New User Bonus. T&Cs Apply.
DraftKings Promo: Bet $5 Get $200
PLUS $50 Bonus Bet On Deposit
PLUS Up to $1,000 Deposit Bonus
Gambling Problem? Call 1-800-GAMBLER
To Claim: Click Bet Now
UP TO $1,250
On Caesars
Stream NFL Games In App For Free
+ Get 1,000 Caesars Reward & $1,000 Tier Credits
Redeem for Bet Credits, Hotel Stays, & More!
Use Promo Code: LEGALFULL
No Sweat First Bet
Up to $2,500 No Sweat First Bet
Available on iOS, Android & Desktop
To Claim: Click Bet Now
Bet $1
GET $200
In Bonus Bets
Bet $1, Get $200 Win or Lose
Sign Up, Deposit and Play Today in VA!
Gambling Problem? Call 1-800-Gambler 21+ 
To Claim: Click Bet Now
Brett Gibbons Avatar
Written by
Brett Gibbons

Brett is an avid sports traveler and former Division-I football recruiter for Bowling Green and Texas State. He’s a graduate of BGSU and works as an auditor for Google content curation products. He’s also contributed to Sports Illustrated and Fansided during his young writing career.

View all posts by Brett Gibbons