The Cheltenham Gold Cup is a race where legends are crowned, but not every champion enters the festival as a favorite. While dominant horses like Arkle, Best Mate, and Kauto Star have stamped their authority on the race, some of the most thrilling Gold Cup moments have come from unexpected winners who defied the odds.
From outsiders who stunned the racing world to novices who rewrote history, these are the greatest underdog victories in Cheltenham Gold Cup history.
1. Coneygree (2015) – The Novice Who Shocked the Racing World
One of the most historic and surprising Gold Cup victories came in 2015, when Coneygree became the first novice to win the race in over 40 years.
Why It Was an Underdog Story:
- Novices rarely run in the Gold Cup, let alone win it.
- Coneygree had run just three times over fences before the Gold Cup—one of the least experienced chasers in history to enter the race.
- He took on seasoned Grade 1 winners like Silviniaco Conti and Road To Riches, yet dominated from the front.
How He Won:
Trainer Mark Bradstock and jockey Nico de Boinville employed fearless front-running tactics, setting a relentless gallop from the start. Many expected him to fade up the Cheltenham Hill, but instead, he powered on to victory, winning by 1½ lengths.
Coneygree’s triumph proved that novices could still take on the best and win, changing the way trainers approach young chasers.
2. Norton’s Coin (1990) – The Biggest Gold Cup Upset of All Time
If there was ever a true fairy tale moment in the Cheltenham Gold Cup, it came in 1990, when Norton’s Coin stunned the racing world by winning at 100/1, making him the biggest-priced winner in Gold Cup history.
Why It Was an Underdog Story:
- Trained by Sirrell Griffiths, a dairy farmer from Wales who had just three racehorses in his yard.
- Norton’s Coin was entered at the last minute, only because Griffiths decided against running him in a handicap race.
- The field included Desert Orchid, the 1989 champion and one of the most beloved racehorses of all time, who was heavily favored to win again.
How He Won:
Despite being overlooked by bookmakers and racing analysts, Norton’s Coin tracked the leaders and surged ahead late, beating Toby Tobias and Desert Orchid in a stunning finish.
His victory remains one of the greatest shocks in Cheltenham Festival history, proving that small stables can still take on and defeat the sport’s biggest names.
3. L’Escargot (1970 & 1971) – Beating the Superstars
Before L’Escargot won his first Cheltenham Gold Cup in 1970, the racing world had already crowned Arkle (1964-1966) and Mill House (1963) as the greatest stayers of the era. But few expected an Irish outsider to rise to the top.
Why It Was an Underdog Story:
- Trained in Ireland by Dan Moore, who was competing against powerhouse British yards.
- Was often overlooked in favor of more dominant English-trained stayers.
- Won back-to-back Gold Cups in 1970 and 1971, proving his class and staying power.
How He Won:
L’Escargot ran a perfectly judged race, outstaying the competition and confirming his greatness with a repeat win the following year.
But his underdog story didn’t end there—he later went on to win the Grand National in 1975, famously defeating the legendary Red Rum, making him one of the most versatile stayers in history.
4. The Thinker (1987) – Conquering the Elements
The 1987 Cheltenham Gold Cup was unlike any other—the race was run in blizzard-like conditions, with snow falling heavily throughout the contest. It was in this chaotic setting that The Thinker emerged as an unlikely champion.
Why It Was an Underdog Story:
- Trained in the north of England, which was rare for Gold Cup winners at the time.
- Entered the race as a longshot, with the spotlight on more well-known chasers.
- Had to handle treacherous race conditions that left many top horses struggling.
How He Won:
The Thinker handled the heavy ground better than his rivals, storming through the snow to claim an unlikely Gold Cup victory, proving that determination and adaptability can overcome any obstacle.
5. Cool Dawn (1998) – The 25/1 Longshot That Stunned Cheltenham
When Cool Dawn lined up for the 1998 Cheltenham Gold Cup, few believed he had a realistic chance of winning. With questionable stamina and a tendency to make jumping mistakes, he wasn’t seen as a serious contender.
Why It Was an Underdog Story:
- Entered the race at 25/1, with most experts doubting his ability to last the distance.
- His owner, Didi Whitbread, was an amateur rider who had originally bought the horse for hunting!
- The race was stacked with stronger contenders, but Cool Dawn showed remarkable grit.
How He Won:
Despite an early jumping mistake, Cool Dawn battled his way through the field, fending off Florida Pearl to win by a narrow margin.
His story is a reminder that in racing, passion and perseverance can defy all odds.