Every March, there are four days that send a ripple through the racing world. For punters, owners, and anyone daring to dream, the Cheltenham Festival sits right at the summit of the jumps season. It’s when the roar spills down from Cleeve Hill and one well-timed stride can turn a small each-way punt into a story that lives on for years.
Down the years, Prestbury Park has produced scenes that go far beyond sport. Fairytales. Gut-wrenching heartbreak. Moments of sheer brilliance that cement the Cotswolds as the true spiritual home of National Hunt racing.
So, as we toast the blue riband contests, we’ve pulled together the very best of them — the days that had bookmakers sweating and punters either floating on air or staring into the abyss.
This is our definitive countdown of the Top 10 Cheltenham Festival Moments.
10. The Machine That Refused to Break (Sprinter Sacre, 2016)
The unbeatable champion of 2013, the horse who had slammed Sizing Europe by 19 lengths in the Queen Mother Champion Chase, had suffered heart issues and a bleak spell. But in 2016, Sprinter Sacre returned to the scene of his former glories.
Under a cool ride from Nico de Boinville, the 10-year-old showed confidence, jumping his rivals into submission.
9. The Amateur Who Beat the Pros (Long Run, 2011)
In the modern era of clinical professionalism, amateur jockeys aren’t supposed to win the Cheltenham Gold Cup. Someone forgot to tell Sam Waley-Cohen. Riding the French-bred Long Run, who is a dentist by day.
Cruising down the hill, Waley-Coven delivered the ride of a lifetime, jumping the last upsides and striding away to land the biggest prize of all.
8. The Five-Horse Trick (Michael Dickinson, 1983)
In 1983, trainer Michael Dickinson saddled the first five horses past the post in the Cheltenham Gold Cup. This includes:
- Bregawn
- Captain John
- Wayward Lad
- Silver Buck
- Ashley House
Filled the places in that order, a feat of training prowess that has never been remotely threatened since. It was less a horse race and more a Dickinson procession, leaving the racing world and the bookies utterly speechless with Cheltenham accumulators crumbling all over the country.
7. The 100/1 Fairytale (Norton’s Coin, 1990)
If you like betting on underdogs, you need to stand up for Norton’s Coin. This was the ultimate outsider story. Trained by Welsh dairy farmer Sirrell Griffiths, who had just three horses and drove the winner to the track himself. The 100/1 shot walked into the Gold Cup enclosure to face the mighty Desert Orchid.
Against every law of racing physics, Norton’s Coin powered up the hill to land the biggest upset in Festival history.
6. The Greatest Punt Saved (Annie Power, 2015)
This one makes the list not because of a win, but because of a loss that spared the betting industry an absolute hammering.
Heading into the final race, punters had been on a tear. Short-priced favourites had been obliging all afternoon, accumulators were stacking up nicely, and bookmakers were staring at what could’ve been a brutal payout. Then came Annie Power — the supposed banker in the Mares Hurdle, the one everyone labelled a good thing.
5. The Return of the King (Kauto Star, 2009)
The rivalry between Kauto Star and Denman is the stuff of boxing matches, not horse racing. In 2008, “The Tank” Denman had humbled Kauto in the Gold Cup. A year later, Kauto Star returned as the NAP for the rematch. He was looking to make history, aiming to become the first horse ever to regain the Gold Cup.
Under Ruby Walsh, he produced a flawless display of jumping to beat his old rival decisively. It was a victory of redemption, silencing the critics and cementing his legacy as one of the true greats. For punters who stuck with him, the 5/1 odds felt like stealing.
4. The Tears for a Trio (Best Mate, 2002-2004)
Best Mate, the people’s champion, brought sheer joy to the Cotswolds. Trained by the effervescent Henrietta Knight and ridden by Jim Culloty, the Irish-bred star delivered three consecutive Gold Cup victories from 2002 to 2004.
The third win was the stuff of legend. As he was cheered up the hill by a crowd fighting back tears, Best Mate became the first horse since the mighty Arkle to achieve the hat-trick.
3. The Ride of the Century (Wichita Lineman, 2009)
Riding Wichita Lineman in the William Hill Trophy Handicap Chase, McCoy was on a horse that looked distinctly unenthusiastic. At the third-last fence, he made a horrific mistake, leaving the jockey with a mountain to climb and a dozen horses to pass.
What followed was a demonstration of sheer force of will. McCoy cajoled, pushed, and physically dragged his partner up the infamous hill to snatch victory by a neck. It was described as “the greatest ride in Cheltenham history,” a moment that defined the 20-time champion jockey’s iron will.
2. The Unconquerable ‘Himself’ (Arkle, 1964-1966)
To understand Cheltenham, you must understand the shadow cast by Arkle. Widely regarded as the greatest steeplechaser of all time, and dominated the Gold Cup for three consecutive years in the mid-60s.
His 1964 victory over the reigning champion Mill House was billed as the “race of the century,” and Arkle won it with such contemptuous ease that he instantly became a national hero.
1. The Mare Who Conquered All (Dawn Run, 1986)
If there is one moment that encapsulates the heart-stopping drama of Cheltenham, it is Dawn Run in 1986. Having already won the Champion Hurdle two years prior, the Irish mare lined up for the Gold Cup, aiming to become the first horse ever to complete the double.
Ridden by the late, great Jonjo O’Neill, she looked beaten jumping the last. But in front of a delirious crowd, she dug deeper than any horse should. To this day, it remains the greatest training feat in Festival history.
Final Thoughts
For punters, these moments are more than just history—they’re the reason we brave the morning rush to the bookies. They remind us that form books can be torn up, that a 100/1 shot can make a dairy farmer a legend, and that a single fall can break a million accumulators.
As you study the card for next week, remember that you’re not just betting on horses, you’re betting on stories. Here’s to finding your own Dawn Run, and to making the hill your own.
Related: The Biggest Cheltenham Festival Accumulators Ever Landed (100/+ Shocks)