The most iconic Cheltenham Festival Gold Cup moments and winners
With the 2026 Cheltenham Festival and the feature race of the week, the Gold Cup, around the corner it’s vital to look back at some of the best moments and Gold Cup wins in recent years.
The 2026 Gold Cup could be the most unpredictable for some years but that’s often been the case for this incredibly tough and rewarding race.
Horse racing is a sport steeped in history so it makes choosing the best moments a bit tricky to cover centuries of winners.
The first Cheltenham Gold Cup was held in 1819 as a flat race over 3 miles.
The race we know now as a jumps contest over fences, wasn’t seen until 1924 and quickly became a staple in horse racing to be amongst the biggest races each season.
From ‘Dessie’ to Rachael Blackmore, there are some incredible names on this list.
Dessie’s desire to victory
The rain had hammered down in 1989 meaning the Gold Cup renewal was set for some very testing conditions for the horses on heavy ground.
But that didn’t phase the favourite and popular Desert Orchid, known as ‘Dessie’, who surged through the mud in spectacular fashion.
Not only because of the way he asserted his lead but the grey really stuck out amongst the flying mud.
The horse was ten-years-old at the time, adored by racing fans and a popular punt at 5/2.
But it was the dramatic nature in which he won that really makes this Gold Cup stand out for entertainment intwined.
With three fences to go Desert Orchid was in the lead but was soon headed by Yahoo.
However, the grey captured the audience with his usual exuberant jumping style as he powered through to win on the flat in the final moments of the race, to win by a length and a half.
It was this season that really added to his legendary status and his place in the history books, where his statue is featured prominently at Kempton Park.
Denman vs Kauto Star
We only have to go back to 2008 for another top moment to come from the Cheltenham Gold Cup and that is the iconic Denman vs Kauto Star.
Both horses were big fancies for that Gold Cup, at the top of the market, both from the same stable trained by Paul Nicholls, both eight-years-old and both with every chance.
Kauto Star went into the race as the big odds-on favourite though with a plethora of Grade 1 wins behind him, mostly under jockey Ruby Walsh.
But it was ‘The Tank’ Denman that provided the moment of glory with an incredible run to drive on to the finish under jockey Sam Thomas.
Not only was it a fantastic showing of two of the best chasers at the time but helped towards an historic 1-2-3 for Nicholls, who also had Neptune Collonges place in third just behind them.
It was a show of a combination of everything great about horse racing, entertainment, drama, horsemanship, training performance and determination from animal and rider.
Arkle
It’s so hard for a horse to win the Gold Cup – the course, the distance, the conditions, everything pushes for only the best horse to come out on top on the day.
But it was Arkle who won not one, not two but three Gold Cups in succession between 1964 and 1966 – and the first to do so since Cottage Rake between 1948 and 1950.
Arkle secured the King George VI Chase just three months prior to winning the 1966 Gold Cup at odds of 1/10, the shortest ever price for a Gold Cup winner.
Best Mate
Horse racing fans had to wait until 2004 to see another horse win three successive Gold Cups at Cheltenham.
And that accolade went to Best Mate trained by Henrietta Knight.
Best Mate was also the first horse to win the Gold Cup more than once since L’Escargot who won in 1970 and 1971.
At just seven-years-old the Knight-trained horse attained his first Gold Cup in 2002 at 7/1 under Jim Culloty, who retained the ride each year.
He has etched his name into history and lives on in numerous ways too, with an enclosure at Cheltenham Racecourse named after him as well.
But it was his 2004 historic victory that really shone not just to win three in a row but to do so in the manner he did on the day.
Best Mate was fourth going into the fourth fence from the finish, but looked poised to challenge.
After the third fence four horses went close together where Best Mate looked to be boxed in and short of room.
For many horses that would be the race finished but Best Mate kept going and at the second last jumped through in front with a surge of speed.
He had to really hold on to that lead and he did so just half a length ahead of Rembrandt in second and Harbour Pilot who made it a battle to the line.
History making Rachael Blackmore
It’s difficult for anyone to think of modern day Cheltenham Festival Gold Cups and not think of the history making ride from Rachael Blackmore in 2022.
In all of the runnings of the Gold Cup over fences, no female jockey had ever won the prestigious race, until Blackmore rode A Plus Tard to victory.
Better still she did so by beating the previous year’s winner Minella Indo, by a staggering 15 lengths!
Blackmore had huge success at Cheltenham Festival in 2021 with six winners before then going on to win the Grand National in what can only be a complete dominance of the biggest races in jumps racing.
Blackmore then followed that up with the historic Gold Cup a year later and quickly became a household name.
100/1?!
Just a year after Dessie’s victory in the Gold Cup, racing fans were treated to another dramatic finish.
A rare one at that. It’s unusual for the Gold Cup to offer up a price in the double digits, but more so in the triple.
Norton’s Coin won by 3/4 of a length in the 1990 renewal for trainer Sirrell Griffiths.
Desert Orchid did go for his 2nd Gold Cup crown in as many runs but at 10/11 and at 11-years-old he finished just under five lengths behind the surprise winner.
He never really looked like a 100/1 shot either which was another element to the surprise.
Looked okay on the bend into the final straight, two fences from the finish Norton’s Coin, Toby Tobias and Desert Orchid jumped it together for a three-way fight.
But coming up to the last the grey just faded out slightly and somehow Norton’s Coin managed to eek out a little bit more in the final 100 yards or so for a thrilling finish.
Golden Miller’s famous five
You can’t mention the Gold Cup without also acknowledging the most successful horse of this historic race.
Golden Miller won the Cheltenham Gold Cup five times in consecutive years from 1932 and 1936.
He was just five-years-old when winning his first at 13/2 before justifying favouritism a year later.
Basil Briscoe trained the horse for the first four wins before Owen Anthony took over in 1936.
Amazingly, there were four different jockeys on board the five wins, Ted Leader, Billy Stott, Gerry Wilson (1934 & 1935) and Evan Williams.
This helps to prove just how good the horse was that so many different jockeys could help guide him to victory, all at a variety of prices too!
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