The Biggest Cheltenham Wins & Bets Ever Seen at Cheltenham Festival
The Cheltenham Festival often creates new superstars overnight. After all, the Festival is a place where horses become legends. It’s also a place where jockeys, trainers and owners vie for some of the largest purses in the world of horse racing.
However, it’s not just those on the racecourse who can go from rags to riches at the Festival. In the past, people who have placed big Cheltenham bets have also become millionaires when their horse has crossed the finishing line first.
With this in mind, here’s our guide to the biggest Cheltenham winning bets in history.
The Biggest Wins at Cheltenham
The biggest wins at Cheltenham can be categorised in a number of ways. For some, it’s the biggest overall stake. For others, it’s the longest odds or the greatest upsets. For us, the biggest wins at Cheltenham are all about cold, hard cash. As a result, we did some digging and tried to unravel the many layers of secrecy and mystery to uncover the biggest cash wins in Cheltenham history.
So, without further ado, here are the biggest Cheltenham winning bets of all time, ranked in order of how much money they (reportedly) earned the lucky punter.
On the opening day of the 1991 Cheltenham Festival, the bookies took a real hit when Destriero caused a major upset in the Supreme Novices’ Hurdle.
In the leadup to the Festival, owner Noel Furlong had attempted to keep the horse’s talent under wraps. So, despite winning on his debut at Leopardstown in January 1990, Destriero didn’t run again until December of that year.
As a result, he was ignored by many punters and was almost at double-digit odds when ante-post betting opened. Furlong was undeterred and placed £300,000 of wagers down at the 6/1 starting price.
When Destriero romped to victory, Furlong’s bets returned a rumoured £1,500,000. Today, we think this remains the biggest win at Cheltenham in history.
Somewhat comically, Furlong was brazen when asked why Destriero hadn't been more active in the lead-up to Cheltenham. The Irishman replied that he was deliberately held back, explaining: "We didn’t run him [again] because we didn’t want to end up getting 2/1 instead of 6/1."
2) Conor Murphy - 2012 Acca - £1,000,000… but it could have been more
In 2012, stable lad Conor Murphy became a millionaire after landing a life-changing bet. At a whim over Christmas 2011, he placed a five-fold acca for £50 that included five horses that were trained by his boss, Nicky Henderson. To his surprise in March, the winners kept rolling in. He backed:
The only downside is that Murphy thought he was able to claim a whopping £3 million in winnings. But sadly, Bet365’s maximum payout was £1 million. Not bad, but it’s difficult to not think about what might have been.
3) Tim Kilroe - Forgive n’ Forget, 1983 Coral Golden Hurdle - £1,000,000
Long before the days when an online tip could cause the market to shift, Tim Kilroe hatched a plan that would eventually net him a rumoured £1,000,000.
After buying Forgive n’ Forget from seller Barney Curley, he kept his cards close to his chest and didn’t let the rest of the racing world know of the horse’s true pedigree.
By the time of the 1983 Coral Golden Hurdle, Forgive n’ Forget was well known enough to be carrying the second-highest weight. But, he initially attracted double-digit odds because of this.
Billed as a ‘licence to print money’, the punters flocked to Forgive n’ Forget in numbers and he ultimately went off at 5/2. The bookies were shocked (and a little out of pocket) when he won comfortably.
Two years later, he proved it was no fluke by winning the Gold Cup. Unsurprisingly, the odds weren’t as kind that time around!
4) JP McManus - 2006 Cheltenham Festival - £925,000
Back in 2006, it’s rumoured that legendary racehorse owner JP McManus took almost £1,000,000 from a single bookmaker in one day of racing at the Cheltenham Festival.
Feeling bullish, McManus approached ‘Fearless’ Freddie Williams, a Scottish bookie who specialised in high-stakes bets. He then put £100,000 on his own horse, Reveillez, at 6/1 in the Jewson Novices Handicap Chase, the first race of the day.
When the surprise win came in, McManus was left with £600,000 in profit. However, unhappy with his winnings, he went back to place £5,000 each-way on Kadoun in the Pertemps Final Handicap Hurdle at 50/1.
Astoundingly, this bet also came in, leaving Williams forking out another £325,000 to McManus.
5) Phil Williams - Son of Flicka, 2012 Coral Cup - £900,000
Many professional athletes struggle to recapture the highs of their playing days after they’ve retired. However, the opposite is the case for former Arsenal, Wigan and Crewe footballer Phil Williams.
A self-confessed ‘punter for all my life’ and the owner of the horse in question, the former midfielder lumped on Son of Flicka in the 2012 Coral Cup. He placed his first ante-post bet at 66/1 and saw the horse’s price drop as low as 16/1 at post (perhaps partially influenced by the value of his own bets).
When Son of Flicka crossed the line 3.5 lengths clear a few minutes later, he was £900,000 richer.
Big Bets at Cheltenham Recently
In recent years, betting at the Cheltenham Festival has been more popular than ever. While many of us are happy staking a couple of pounds on the outcome of a race, some people are so certain of their tips that they’re willing to place incredibly big bets at Cheltenham. With this in mind, here are two big Cheltenham bets from last year’s Festival:
Tony Bloom - £400,000 - Energumene, 2023
Tony Bloom, the owner of Brighton & Hove Albion Football Club, reportedly won big in 2023 when he backed his own horse, Energumene, in the Champion Chase.
After Energumene’s win, Bloom confessed that he’d “had a few quid” on the horse. His usual bookie, Star Sports, reported they took a £400,000 bet on the 6/5 favourite that returned £580,000, including stake.
Unknown - £230,000 - Constitution Hill, 2023
At the 2023 Cheltenham Festival, one lucky punter was so certain that Constitution Hill would triumph in the Champion Hurdle that they placed almost a quarter of a million pounds on the outcome.
The unknown gambler, who placed their bet with Brighton-based bookie Star Sports, placed £230,000 on Constitution Hill to win the race at 4/11. When he romped home, the punter was £83,636 better off.
Our Cheltenham Tips
Thinking about placing a bet on the action at Cheltenham yourself this year? Take a look at our tips for the Festival. To help make choosing your selections as easy as possible, we’ve also created detailed guides for each day of action:
