Pots of Gold! The five biggest priced winners of the Cheltenham Gold Cup

Tom Reed
9 March 2023

Jockey Davy Russell celebrates victory on Lord Windermere with winning connections including Lord Windermere with Tom Doyle (far left), Peter Dooley (centre right) and trainer Jim Culloty (fa

The Cheltenham Gold Cup is the glittering prize for the best chaser in jumps racing but not every winner is well fancied in the betting.

Planet Sport takes a special look at the biggest outsiders to have run away with the Cheltenham Gold Cup since its inception in 1924.

Gay Donald (1955) 33/1

A friendly, quirky horse, Gay Donald had a cloudy eye after an injury at birth - it also had a penchant for Liquorice Allsorts and sardine sandwiches. However, that wasn't enough to stop him from storming to a big price win in the 1955 Gold Cup.

Jockey Tony Grantham rode the Queen's first winner as a racehorse owner, but he was unfancied on the Jim Ford trained Gay Donald. Reigning champ, Four Ten, led the market at 3/1.

10th Mar 1955 @CheltenhamRaces
Mr Philip Burt's Gay Donald & Tony Grantham, takes the last fence before winning the @cheltenham Gold Cup pic.twitter.com/TQfeS9Gk6o
— Anaglogs Daughter (@AnaglogsDaughtr) October 26, 2017

Nevertheless, Gay Donald - the horse with odds over ten times the favourite - took to the wintry conditions at Cheltenham the best, drawing well clear to take the coveted Gold Cup by a solid ten lengths from Halloween.

Gay Donald might have celebrated with his favourite sandwiches but the result certainly left a sour taste in the mouths of favourite backers as Four Ten trailed home in third place.

L'Escargot (1970) 33/1

The horse that went on to halt Red Rum's bid for three Grand Nationals on the spin made his name winning a pair of Cheltenham Gold Cups in the early 1970's.

L'Escargot - named after a snail - was no slouch, crossing the Atlantic to win the Meadow Brook Steeplechase at Belmont Park in the USA in 1969.

Tommy Carberry up on L'Escargot taking a fence during the Cheltenham Gold Cup

The horse's American adventure saw L'Escargot fly under the radar when setting out for the 1970 Gold Cup. He was priced at a huge 33/1.

However, when the race started, it was clear L'Escargot had been overpriced, taking advantage of a fall by the hot favourite Kinloch Brae and then engaging in a toe-to-toe tussle with French Tan over the final fence.

French Tan jumped better but L'Escargot's jockey Tommy Carberry showed great grit and rallied his mount for a length and a half victory.

Punters who had taken the 33/1 bet proceeded to collect their winnings at considerably faster than a snail's pace. L'Escargot came back the next year and won again at a measly 7/2.

Norton's Coin (1990) 100/1

Legend has it that Tim Jones, the amateur jockey that rode Norton's Coin in his early hunter-chases, announced at a dinner dance in 1988 that the horse would win a Gold Cup.

Few rated the value of Norton's Coin, the horse owned and trained by Welsh dairy farmer Sirrel Griffiths, who only had two other horses in his stable.

Cheltenham Gold Cup winner Norton's Coin, with jockey Graham McCourt celebrating, as they arrive in the winner's enclosure

Yet, such is the unpredictability of horse racing that sometimes champions arrive from humble beginnings and Norton's Coin was certainly ready to spin the 1990 Cheltenham Gold Cup on its head.

In his way was the front running fans-favourite Desert Orchid. Nevertheless, jockey Graham McCourt was happy to stalk "Dessie" and produce a challenge from two out.

Norton's Coin took a clever path between Desert Orchid and 8/1 shot Toby Tobias to pull ahead for a three-quarter length win.

Afterwards, the dairy farmer winning trainer Griffiths wasn't one to milk the victory. They had shaken up the racing establishment with the largest winning price winner in Cheltenham history that is unlikely to be beaten.

Cool Dawn (1998) 25/1

The head of the NHS Test and Trace coronavirus response team, Dido Harding, hit the headlines in 1998 as owner of the Cheltenham Gold Cup horse Cool Dawn.

Cool Dawn's record in racing can be traced back to Point to Point races in Ireland, climbing the ladder, rung by rung, via a second in the 1996 Foxhunter Chase at Cheltenham under Harding herself.

Cool Dawn ridden by Andy Thornton clears the second fence en route to victory in the Tote Cheltenham Gold Cup at Cheltenham

The keen amateur jockey Harding entrusted Cool Dawn, a 25/1 Chance for the 1998 Gold Cup, to jockey Andrew Thornton.

Cool Dawn had ten horses ahead in the betting, including Paul Nicholls' See More Business and the favourite Dorans Pride, trained by Michael Hourigan.

However, Thornton hadn't read the script and sent Cool Dawn on a front running ride, using the jumping skills honed on the point-to-point circuit to deadly effect.

With See More Business carried out by a pulled-up horse, all Cool Dawn had to do was lead from the front and invite mistakes from Dorans Pride, a plan which worked to perfection for a one and three quarter length win.

The 25/1 price was as cool as the winner's moniker.

Lord Windermere (2014) 20/1

Maybe it was a case of trainer Jim Culloty being unfashionable compared to the might of opponent handlers Paul Nicholls and Nicky Henderson but Lord Windermere was a damned sight better than his 20/1 price.

In one of the most dramatic Gold Cup finishes ever seen, Davy Russell prevailed in a contentious finish that went to a steward's enquiry.

Jockey Davy Russell kisses The Betfred Cheltenham Gold Cup after winning onboard Lord Windermere

With former winner Bobs Worth and the fancied Silviniaco Conti veering left and then Lord Windermere swerving right it was left to the stewards to decide a messy race that saw Russell get up in the purple and yellow silks by a short-head from On His Own.

After a 15 minute deliberation, Lord Windermere was awarded the race, making Culloty only the fourth horseman to win the Gold Cup both as jockey and trainer.

There were deep discussions about the validity of the Gold Cup win of the horse named after the great lake. Nevertheless, Lord Windermere went down as the biggest priced winner since Cool Dawn and provided a feather in the cap for Culloty's modest training operation in the face of the big boys.