Kentucky Derby: Biggest Underdog Winners And Betting Tips
- The biggest Kentucky Derby underdog winners over the years
- How to spot Kentucky Derby underdogs with the help of our betting tips

The Kentucky Derby is one of the most high-profile races in the world, and some iconic winners and mega-bucks have been made over the years.
Our team of experts at JustGamblers has done some digging to highlight some of their favorite biggest Kentucky Derby winners over the years.
We have also added some top tips for those placing bets on this event—check it out!
1. Donerail in 1913 — Odds: 91-1
Donerial was an American Thoroughbred racehorse and was the upset winner of the 1913 Kentucky Derby.
His win is the biggest longshot victory in history, with odds of 91–1. Those placing as little as $2 on Donerail would receive a nice $184.90 payoff. Adjusted for inflation, this would amount to $5,870.95 in 2024.
Ten Point, the favorite, was still leading in the 1913 race as the horses turned into the last stretch, but Donerail closed to gain the lead, crossing the wire half a length ahead of Ten Point. Donerail not only won but set a track record with a time of 2:04 4/5.
2. Rich Strike in 2022 — Odds: 80-1
Finally, 2022's shocking underdog was Rich Strike, with a finishing time of 2:02.61. At 80-1, he had the longest odds amongst the 20 competing horses at the Kentucky Derby.
Rich Strike was purchased for just $30,000, and with his win, he took home $1,860,000 of the Kentucky Derby’s $3 million purse.
It was also a first win for the trainer Eric Reed and jockey Sonny Leon.
3. Country House in 2019 — Odds: 65-1
Country House upset in 2019 was particularly upsetting because the horse Maximum Security crossed the finish line first but was later disqualified for interference.
Country House’s jockey, Flavien Prat, immediately made an objection call, accusing jockey Luis Saez of interfering with several horses down the final stretch. The interference did not impact him and his horse, but the objections were valid, and their second placement turned into a first place and the third biggest Kentucky Derby upset.
4. Giacomo in 2005 — Odds: 50-1
Giacomo entered the Kentucky Derby in 2005 with only one win, not even close to being a co-favorite.
Owned and bred by music executive Jerry Moss of A&M Records, Giacomo defied all odds and accomplished his first derby win through a blanket finish. He gained speed down the stretch and just barely made it for a three-horse photo finish.
5. Mine That Bird in 2009 — Odds: 50-1
In 2009, Mine That Bird came seemingly out of nowhere down the final straight to position himself along the inside of the track.
Pulling away, he won by six and ¾ lengths, the highest margin of victory in over 60 years. He ran the Derby's mile-and-a-quarter distance in 2 minutes and 2.66 seconds.
6. Charismatic in 1999 — Odds: 31-1
Charismatic took fans on an unforgettable journey through the Triple Crown trail in 1999 to overcome the 31-1 odds as he and jockey Chris Antley stormed the field and emerged victorious.
Charismatic mocked the owners who spent millions of dollars in the quest for a Kentucky Derby winner, as his pricetag was as low as $62,500.
Five Betting Tips For Spotting Kentucky Derby Underdogs Before the Race Starts
- Favorites tend to dominate, but don’t underestimate potential Kentucky underdogs
Over the years, favorites have dominated the Kentucky Derby.
However, as this list of Kentucky underdog winners shows, upsets happen and spotting them can lead to massive payouts that’d make up for all the missed underdog bets leading up to the big win.
Never underestimate the unexpected at the Kentucky Derby.
- Check past performances and Derby prep races
You’ll learn much by researching and analyzing previous races, particularly Kentucky Derby prep races. Don’t just look for winning results but general placements. Perhaps you’ll spot a horse with high average placements and some near wins, which could spell underdog potential.
- Ignore the media and the hype
Successful Kentucky Derby bettors don’t read the headlines from the media’s top betting “experts.” These so-called experts tend to focus on one or two horses to drive their narrative, which skews the reality of the race. Instead, do independent research on the horses and races and put faith in advice from real experts that contribute to alternative channels outside mainstream media.
- Avoid horses who ran more than three times between January and April
Horses who race too often during the winter and spring tend to be disadvantaged.
Therefore, it is best to opt for a horse in peak form. Between 2005 and 2018, every Kentucky Derby winner competed in just two or three races between January and April of their 3-year-old seasons.
- Consider other betting options outside winner bets
While you shouldn’t go crazy with exotic bets, there are a couple of markets you should consider, mainly place bets and show bets. These bets allow you to wager on potential Kentucky Derby underdogs that can finish first or second in the case of place bets and if a horse will finish in the top three in the case of show bets.
“Bonus advice from me, which may contradict this article. Don’t ignore the favorites. The truth is that favorites win around one-third of all horse races. If you’re doing your homework ahead of the Kentucky Derby and find that your research strongly suggests that the favorite of the race is going to win, then go ahead and bet it if you think there’s value in the wager.”
— Patrik Lidin, Head of Content at JustGamblers.
Share Your Thoughts!
We hope you found our look at the biggest Kentucky Derby winners and our betting tips insightful. Now it's your turn!
Do you have any betting strategies or memorable Derby moments to share? What are your predictions for the upcoming races?
We’d love to hear your thoughts and experiences!