In turf horse racing, anything can happen. That’s part of what makes the sport so thrilling not just for spectators, but for bettors, trainers, and jockeys as well. Despite the best predictions, careful form analysis, and favored entries, underdogs can and do pull off stunning victories, often turning the racing world upside down.
Over the years, there have been several unforgettable moments when longshots stole the spotlight and shocked both fans and bookmakers. In this article, we revisit some of the biggest upsets in turf horse racing history races where expectations were shattered and legends were born.
1. Norton’s Coin Cheltenham Gold Cup (1990)
- Odds: 100/1
- Race Type: Turf, National Hunt
- Location: Cheltenham, United Kingdom
While technically a steeplechase, Norton’s Coin delivered one of the most shocking upsets on turf when he won the 1990 Cheltenham Gold Cup, defeating some of the greatest jumpers of the era. Trained by a dairy farmer in Wales, Norton’s Coin was barely considered a contender but he stunned the crowd by overtaking the favorite, Desert Orchid, and clinching victory in one of the UK’s most prestigious races.
2. Motivator vs. Wings of Eagles Epsom Derby (2017)
- Odds: 40/1
- Race Type: Turf, Flat
- Location: Epsom Downs, United Kingdom
Wings of Eagles came into the 2017 Epsom Derby as a virtual unknown, overshadowed by stablemates with much higher expectations. With a late burst of speed in the final furlong, he surged past the favorites and claimed one of the most unexpected Derby wins in modern history.
3. Arcangues Breeders’ Cup Classic (1993)
- Odds: 133/1 (U.S. $269.20 for a $2 win)
- Race Type: Dirt (originally a turf horse)
- Location: Santa Anita Park, USA
Though technically run on dirt, this is a must-mention due to Arcangues being a proven European turf horse transitioning to dirt a surface he had never raced on. Coming in as the biggest longshot in Breeders’ Cup history, Arcangues shocked everyone by winning the Breeders’ Cup Classic, a feat that still resonates as one of horse racing’s most jaw dropping moments.
4. Prince of Penzance Melbourne Cup (2015)
- Odds: 100/1
- Race Type: Turf, Handicap
- Location: Flemington Racecourse, Australia
The 2015 Melbourne Cup will always be remembered not just for the odds defying victory of Prince of Penzance, but also for making history with jockey Michelle Payne, the first female jockey to win the Cup. Few expected Prince of Penzance to even place, but a perfectly timed ride and a powerful finish turned the race into an unforgettable Cinderella story.
5. Serpentine Epsom Derby (2020)
- Odds: 25/1
- Race Type: Turf, Flat
- Location: Epsom Downs, United Kingdom
Serpentine led from the front and never looked back in the 2020 Epsom Derby, pulling off one of the most dominant upsets in recent turf racing history. With little fanfare before the race, many thought he was only in the field as a pacemaker. But the Aidan O’Brien trained colt outpaced all competition to win by over five lengths, shocking bettors and experts alike.
6. L’Emigrant French 2000 Guineas (1982)
- Odds: 33/1
- Race Type: Turf, Flat
- Location: Longchamp, France
In a highly competitive field filled with favorites, L’Emigrant came from nowhere to claim victory in the Poules d’Essai des Poulains (French 2000 Guineas). His stunning late kick left seasoned racing fans stunned and turned the unheralded colt into a national headline.
7. My Tent Or Yours vs. Jezki Champion Hurdle (2014)
- Odds (Jezki): 9/1
- Race Type: Turf, Hurdles
- Location: Cheltenham Festival, United Kingdom
Though not the longest odds on this list, Jezki’s win over My Tent Or Yours and other major favorites was a shocker due to the quality of the field and the sheer competitiveness of the race. It was also a victory filled with emotion, as it gave trainer Jessica Harrington her first Champion Hurdle title.
Why Turf Racing Is So Prone to Upsets
Turf racing, more than any other surface, often produces unpredictable outcomes. Here’s why:
- Variable ground conditions (firm, soft, heavy) impact performance.
- Tactical races favor horses with smart jockeys, not just raw speed.
- Track configurations vary greatly some tighter, some with longer stretches.
- Large, international fields increase competition and variance.
All of this makes turf racing thrilling and full of potential for shocking finishes.
Final Thoughts
The unpredictability of turf racing is what makes it so captivating. While favorites often win, history shows us time and again that the underdog can rise, delivering unforgettable moments and massive payouts. These upsets aren’t just anomalies they’re proof that in horse racing, anything is possible. Whether you’re a racing enthusiast, a bettor, or just a fan of a good underdog story, the world of turf racing offers endless drama, excitement, and surprise. The next big upset could be just one race away.
