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The Cheltenham Gold Cup stands as National Hunt racing’s ultimate examination, where legends are forged and dynasties established.
The Cheltenham Gold Cup represents the pinnacle of achievement in National Hunt racing, a contest where legends are forged and history is written. In the modern era, the Gold Cup continues to captivate audiences worldwide, combining the raw athleticism of thoroughbred racing with the tactical nuance that only three miles and two furlongs of Prestbury Park’s undulating terrain can demand.
As Galopin Des Champs prepares to pursue a historic hat-trick and etch his name alongside the immortals of steeplechasing, racing enthusiasts are reminded that the greatest drama often emerges when champions appear most invulnerable.
While the betting markets signal another coronation for Willie Mullins’ star chaser in the Cheltenham Gold Cup 2025 odds, the unpredictable terrain of Prestbury Park has humbled favourites and crowned unlikely heroes throughout its storied history.
Every outsider has his day and there is always a chance of an underdog story. In this article, we take a look at three of the most remarkable upsets that have stunned the racing world when they snatched the Gold Cup against the odds at Cheltenham.
Norton’s Coin (1990) – The Welsh Wonder
In perhaps the greatest Gold Cup shock of all time, Norton’s Coin delivered a performance that defied both logic and the horse racing betting market.
Trained by Welsh dairy farmer Sirrel Griffiths with just three horses in his yard, the 100/1 outsider rewrote the script on a day when the beloved Desert Orchid was expected to defend his crown.
The nine-year-old’s triumph represented more than just a statistical anomaly – it embodied the romance of National Hunt racing.
Against the backdrop of Desert Orchid’s popularity and a quality field, Norton’s Coin produced a display of jumping excellence that left the Cheltenham faithful in stunned silence, creating an upset that still resonates more than three decades later.
Lord Windermere (2014) – A Hill Too Far for the Favourites
Jim Culloty’s Lord Windermere provided another reminder of the Gold Cup’s capacity for drama with his 20/1 victory. On a day when established stars Bobs Worth and Silviniaco Conti were expected to dominate, Davy Russell orchestrated a masterclass in patient riding.
The stamina-sapping conditions proved decisive as Lord Windermere, seemingly outpaced for much of the contest, found reserves of courage up the infamous Cheltenham hill.
His narrow victory over On His Own showcased the unique demands of the Gold Cup, where reputation counts for little against raw determination and tactical brilliance.
Al Boum Photo (2019) – Breaking the Mullins Hoodoo
While a Willie Mullins-trained winner might rarely qualify as a shock, Al Boum Photo’s 12/1 triumph carried its own weight of historical significance.
After six runner-up finishes in jump racing’s blue riband event, Mullins finally conquered his Gold Cup curse through his perceived third string.
Under Paul Townend’s expert guidance, Al Boum Photo produced a performance of metronomic jumping efficiency, outlasting market principals Presenting Percy and Clan Des Obeaux. The victory, achieved against more fancied stablemates, demonstrated that even racing’s most powerful yards can find glory in unexpected quarters.
