The Cheltenham Gold Cup is not just the highlight of the Cheltenham Festival—it’s one of the biggest betting events in horse racing. Every year, millions of pounds are wagered on the Festival’s flagship race, with punters trying to predict whether the favorite will deliver, an outsider will shock the world, or an each-way bet will bring a solid return.
Over the years, betting trends have evolved, shifting with changing race dynamics, market strategies, and legendary upsets. From banking on short-priced favorites to cheering for long-shot winners, the Gold Cup has seen remarkable betting stories that have kept the sport unpredictable and exciting.
1. The Shift in Betting Trends: Then vs. Now
Early Years: Backing the Best Stayers
In the early years of the Gold Cup, betting was focused on proven stayers, with punters favoring repeat winners like Golden Miller (1930s) and Arkle (1960s). The dominance of a handful of top horses meant punters tended to back the reigning champion, expecting them to defend their title.
The Modern Era: Competitive Fields and Market Shifts
More competition in modern Gold Cups has led to bigger-priced winners in recent years, as fields have become stronger. The introduction of novices into the Gold Cup conversation (as seen with Coneygree in 2015) has changed betting patterns, making it riskier to only back seasoned chasers. Punters have also turned to ante-post betting, trying to lock in bigger odds months before the race.
2. The Favorite’s Curse: Do Short-Priced Horses Deliver?
The Cheltenham Gold Cup is one of the most unpredictable races on the calendar, and history has shown that backing the favorite isn’t always a winning strategy.
How Often Do Favorites Win?
Since 2000, only 8 favorites have won, proving that odds-on horses are far from guaranteed. Between 2013 and 2023, only 3 favorites justified their status, highlighting the difficulty of predicting Gold Cup success. Even legendary names like Kauto Star (beaten in 2008), Long Run (defeated in 2013), and Djakadam (second in 2015 and 2016) have shown that being the market leader doesn’t always translate to victory.
The Exceptions: When Favorites Have Dominated
Some favorites have lived up to expectations, rewarding punters who backed them heavily.
Arkle (1964-1966) won three straight Gold Cups as the strongest favorite in history.
Best Mate (2002-2004) proved that some modern favorites can still deliver, winning three consecutive Gold Cups.
Kauto Star (2007 & 2009) was a betting sensation who won twice but also lost as the favorite in 2008 and 2010.
Key Takeaway:
Favorites only win around 40% of the time, so betting purely on the shortest-priced horse isn’t always profitable. Savvy bettors look for value in the market, considering factors like ground conditions, race tactics, and stamina.
3. The Biggest Betting Upsets in Gold Cup History
The Gold Cup has produced some of the biggest shocks in racing history, where long shots defied the odds and made bookmakers celebrate while punters tore up their slips.
Norton’s Coin (1990) – The Ultimate 100/1 Shock
Trained by a dairy farmer, Norton’s Coin pulled off the biggest upset in Gold Cup history, beating the heavily favored Desert Orchid at 100/1. Punters who placed even a small bet on this outsider walked away with huge payouts.
Lord Windermere (2014) – The 33/1 Surprise
Almost nobody expected Lord Windermere to win in 2014, yet he stormed through late to win by a nose, catching punters off guard. Many had backed Bobs Worth (even-money favorite), but he could only finish 5th.
Coneygree (2015) – The Novice That Defied History
Few expected a novice to win the Gold Cup, yet Coneygree led from start to finish at 7/1. His fearless front-running style caught the field off guard, and punters who backed the novice were handsomely rewarded.
Key Takeaway:
Gold Cup history proves that outsiders can and do win. While it’s tempting to stick with big names and favorites, smart punters keep an eye on well-trained long shots with stamina and strong form.
4. Betting Strategies for the Gold Cup
To bet successfully on the Cheltenham Gold Cup, punters must consider several key factors.
Stamina Over Speed
Many past winners, like Native River (2018) and Denman (2008), were stamina-based horses who excelled in tough conditions. Horses that fade in testing conditions or struggle with Cheltenham’s uphill finish are risky bets.
Watch the Ground Conditions
Soft or heavy ground often leads to shock winners—horses like The Thinker (1987) and Coneygree (2015) thrived in testing conditions. Good ground favors speedier horses like Kauto Star, so betting strategies should adjust based on the weather.
Consider Each-Way Bets on Outsiders
Many long shots have placed in the Gold Cup, making each-way betting (where your horse can finish 1st, 2nd, or 3rd) a safer option. In big fields, horses priced between 10/1 and 33/1 have often run into the frame, making place bets a strong alternative to backing a favorite outright.
Look for Past Cheltenham Form
Horses that have already won or placed at Cheltenham are often more reliable bets, as they have experience with the unique track and demanding finish. First-time Cheltenham runners often struggle under festival pressure.
