Revisit Some of the Best Cheltenham Festival Moments

Every March, all eyes fall on the Cheltenham Festival.

It’s the first major horse racing event of the year, complete with St. Patrick’s’s Day celebrations and a prize fund that almost reaches £5 million. £625,000 of that fund went to the Cheltenham Gold Cup winners in 2025, but the best winners are those who race into the hearts and minds of fans across the world.

We’ve gathered some of our favourite Cheltenham highlights right here. Whether you’re new to the races or just want a walk down memory lane, this is the place to be.

Behind every classic moment was an army of fans that tried their hand at Cheltenham betting. Now, fans can support horses through sites like ours. If the Gold Cup is coming up, consider Cheltenham Festival betting at MONOPOLY Casino & Sports.

The 1964 Mill House vs. Arkle Race

Since Cheltenham usually runs through St. Patrick’s Day, it has long been the battleground for English and Irish horse trainers. The 1964 Gold Cup was one of the earliest instances where two horse racing legends faced off against one another.

Mill House was a prior champion, born and raised in England, while Arkle was an up-and-coming Irish chaser. Going into the race, everyone wondered which of the two would win. Arkle’s steeplechasing was superior; he sailed over the last fences and beat Mill House by five lengths, making one of the earliest, best Cheltenham Festival moments recorded.

Dawn Run’s 1986 Uphill Climb

The Cheltenham Racecourse is famous for its uphill climb at the end of the race, the steepest in European horse racing. It’s the ultimate endurance test for an already tired horse. You’ll see it a lot when looking at Cheltenham highlights.

This uphill struggle brought us the 1986 Gold Cup. This Dawn Run horse, already famous after her 1984 Champion Hurdle win, hits the hill in third place. Rival horse Wayward Lad is ahead, but then she surges up the final stretch to cross the finish line first. Dawn Run became the first mare racer to secure both the Hurdle and the Gold Cup. No horse racing legends have managed it since.

1989, Desert Orchid Storms Through the Mud

By 1989, Desert Orchid had become Britain’s biggest racer. The grey jump horse had roundly lost that 1984 Champion Hurdle, far behind Dawn Run. Despite suffering at the hurdles, Dessie emerged as one of the better fence jumpers in British horse racing.

Even so, doubts were lingering before the 1989 Gold Cup. Dessie ran poorly in the mud and was up against none other than Yahoo, a mud-loving horse with every racetrack advantage you could think of. That dreaded uphill stretch came and, against the odds, a mud-flecked Dessie charged into one of his best Cheltenham races and put Yahoo in second place.

1990, Norton’s Coin Gives Desert Orchid His Own Medicine

A year later, Desert Orchid went from being an odds breaker to suffering one of the greatest upsets in Cheltenham betting history. Norton’s Coin was a nobody horse, raised and trained by a humble Welsh dairy farmer. Going into the 1990 Gold Cup, a plain chestnut Norton’s Coin was given long-shot odds.

You can probably guess what happened next.

Cheltenham Festival betting had made Dessie the slight favourite. Norton’s Coin stayed in the race through pure stamina as competitors fell away until it was just him, Dessie, and Toby Tobias. When that final half mile came, Norton’s Coin took over while Dessie dropped to third. The unlikely Welsh champion lives on as a reminder that there’s no sure thing in sports betting.

If Norton's Coin has you wondering how betting odds actually work, our sports betting guide is worth a read before your next bet.

Istabraq’s Champion Hurdle Hat-Trick, 1998 - 2000

In three short years, Irish thoroughbred Istabraq became the most accomplished hurdler in modern racing. How? By creating three of the best Cheltenham Festival moments years apart. It started at the 1998 Champion’s Hurdle, where he beat the competition by twelve whole lengths. We hadn’t seen a margin that wide since 1932.

1999 wasn’t as flashy; he cruised to victory by three-and-a-half lengths, barely breaking a sweat. Going into the 2000 Champion’s Hurdle, the pressure was on. The crowd was muted before the last hurdle, before exploding when Istabraq led the race up the hill and secured his historic hat-trick.

Best Mate’s Gold Cup Hat-Trick, 2002 - 2004

Not long after Istabraq’s hat-trick, Best Mate stepped up to become the first modern horse to get a Gold Cup hat-trick, something that hadn’t happened since Arkle’s hat-trick in the ‘60s. Best Mate went into the 2002 Gold Cup as a young upstart, not the favourite, but he won the three-mile chase regardless.

Mirroring Istabraq’s Cheltenham highlights, the second 2002 race was an easy win, 10 lengths ahead of the competition. He made it look easy. Then, in 2004, he rounded the final stretch boxed against the rail. Jockey Jim Culloty forced Best Mate through a small gap in the horses ahead, winning by just half a length.

Denman Powers Through the 2008 Gold Cup

The 2008 Cheltenham Gold Cup had the kind of setup you’d expect from a horse racing film. On one side, you had the speedy French-bred Kauto Star, “The King,” and on the other side, you had the sturdy Irish-bred Denman, “The Tank.” Both went into the Gold Cup at the top of their game.

Kauto Star was the clear favourite ahead of Denman in second. Those odds shortened when star jockey Ruby Walsh had to pick which horse to ride. He chose the glamorous Kauto Star. Hopefuls insisted that The Tank’s stamina could beat out The King’s speed. Denman charged up the hill and won the race a whole seven lengths, entering the book of modern horse racing legends.

Sprinter Sacre Comes Back with a Vengeance, 2016

In 2013, Sprinter Sacre ran one of the most memorable Champion Chases ever, a 19-length lead that earned him a Timeform rating at 192p. This isn’t that story, however. It’s the story of how, after missing the past race season due to heart issues, the sporty Selle Français returned with something to prove.

Despite being second favourite, Sprinter ran the race squarely in the middle of the pack, and even botched a hurdle just three fences from the finish. That made what happened next one of the best Cheltenham Festival moments in the seniors’ Champion Chase. Sprinter ran an impressive comeback, winning by three-and-a-half lengths, regaining the championship and retiring as a winner.

Honeysuckle’s Last Ride at the 2023 Mares’ Hurdle

Another of our more recent and best Cheltenham Festival moments, Honeysuckle stepped onto the racecourse at the grand age of nine. This Brit-born, Irish-trained thoroughbred started the season with her first career defeats. Talk of retirement followed. They decided to put her in one last race, the Mares’ Hurdle, where she started as a joint favourite.

Going into the race, many were anxious that she wouldn’t get the fairytale ending she deserved. Honeysuckle’s last ride became one of the most sentimental Cheltenham highlights when she took it by a length.

When fans fill out their betting slip, these horse racing legends often sit at the back of their mind. They prove that anything can happen, that good horses can win consistently, but complete unknowns can and do give the oddsmakers a shock.

Maybe you want in on the next racing legend. To get started, join MONOPOLY Casino & Sports and bet more confidently with historical articles like this in mind, plus real-time odds tracking, live Cheltenham betting and optional spend limits and session reminders.

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