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Cheltenham Festival: 5 of the Biggest Ever Gold Cup Upsets

Gavin Beech for Bookies.com

Gavin Beech  | 5 mins

Cheltenham Festival: 5 of the Biggest Ever Gold Cup Upsets

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1990 – Norton’s Coin (100/1)

The 1990 edition of the Cheltenham Gold Cup will forever have itself a place in Cheltenham Festival folklore – it was the day Norton’s Coin became racing’s very own David against the Goliath that was Desert Orchid.

The chestnut gelding was one of just two horses trained in Wales by dairy farmer Sirrell Griffiths who had paid £5,000 for him after he won two hunter chases in 1987.


Norton’s Coin made his first start of the 1989/90 season in the King George VI Chase where he trailed in last of six runners and his fortunes didn’t improve when dropped back to two miles in the Victor Chandler Chase the following month.

Despite more encouraging efforts in Cheltenham and Newbury handicaps, Norton’s Coin appeared to have a mountain to climb if he was going to make an impact in any festival contest, let alone the biggest of them all.

But once trainer Sirrell Griffiths realised that he had missed the entry deadline for the Mildmay of Flete Handicap Chase then he had little option but to let him take his chance in the big one, for which he had been entered earlier in the season.

Norton’s Coin was the outsider of the entire field in Gold Cup betting lists but, after a patient ride by Graham McCourt, he was bang in contention coming to the third-last before getting the better of runner-up Toby Tobias in a protracted dual up the hill. The mighty Desert Orchid could finish only third.

1992 – Cool Ground (25/1)

The 1992 Cheltenham Gold Cup was meant to be all about the great Carvill’s Hill, but it wasn’t meant to be for the Martin Pipe trained-hotpot who backed out of contention from the third last.

Despite the absence of the star turn from the finish, a titanic three-way battle ensued from the second-last fence involving The Fellow, Docklands Express and Cool Ground.

It looked like 7/2 second favourite Docklands Express had the upper hand between the final two fences but the French raider couldn’t put the race to bed and the three were almost bang in line as they approached the winning post.

However, a late surge from 25/1 chance Cool Ground up the inside earned him the verdict in what was the most epic of Gold Cup battles.

It was an iconic moment in the career of talented young jockey Adrian Maguire who inspired Cool Ground’s late flourish, while it also played a major part in elevating Toby Balding into the select group of trainers that have saddled the winner of the Champion Hurdle, Gold Cup and Grand National.

1997 – Mr Mulligan (20/1)

Mr Mulligan had let favourite backers down when only second at 11/8 in the 1996 Sun Alliance Chase but the huge horse defied much bigger odds 12 months later when running out a most emphatic 9-length winner of the Cheltenham Gold Cup.

Mr Mulligan’s Cheltenham Festival preparation was anything but ideal – he hadn’t been seen since falling two-out behind One Man in the King George VI Chase at Kempton on Boxing Day.

However, his conqueror that day was by no means a guaranteed stayer over the stiffer Gold Cup trip and a forceful ride by Tony McCoy on Mr Mulligan drew the sting out of the popular grey, whose effort petered out approaching the last.

1997 Cheltenham Gold Cup betting had been headed by 4/1 chance Imperial Call but he was one of six runners not to complete the course.

1998 – Cool Dawn (25/1)

Cool Dawn had looked one of the most progressive staying chasers in the country through the 1997/98 National Hunt season but a high-profile reversal at Sandown in February, where his trainer reported that the gelding had trapped a nerve in his shoulder, meant that he went into the Cheltenham Gold Cup as one of the outsiders.

However, despite only having five weeks to get the 10-year-old back to peak condition, Rober Alner produced his stable star to perfection on the day.

Cool Dawn’s task was made slightly easier when the much-fancied See More Business was dramatically carried out by the pulling-up Cyborgo but he still needed to fend off the challenge of 9/4 market leader Doran’s Pride, who had finished third behind Mr Mulligan 12 months earlier.

However, a mistake three-out put the favourite on the back foot and Cool Dawn, who had been on the front end from the outset under Andrew Thornton, stayed on powerfully up the Cheltenham hill to win by a length and a half.

2014 – Lord Windermere (20/1)

The 2014 renewal of the Cheltenham Gold Cup proved one of the most dramatic in recent memory – and it was also one that wrote the name of Jim Culloty into the history books.

12 months earlier, Lord Windermere had run out an 8/1 winner of the RSA Chase – a race that often points the way to a future Gold Cup star, but festival punters couldn’t have Lord Windermere on their mind after heavy defeats in all of his three starts since that RSA victory.

With most of the focus on established stars like Silviniaco Conti and previous winner Bobs Worth, the Jim Culloty-trained eight-year-old was allowed to go off a relatively unconsidered 20/1 chance in Gold Cup betting lists and for much of the contest those odds looked an accurate reflection of his chance as he trailed the main field for a long way.

However, as the race began to heat up, Davy Russell began to get a good tune out of his mount and a storming late flourish took him past wandering rivals and to a most unlikely success.

Culloty became only the fourth man to both train and ride a Gold Cup winner having steered the imperious Best Mate to a hat-trick of big-race victories, the last of which came exactly ten years earlier.

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About the Author

Gavin Beech for Bookies.com
Gavin Beech
Gavin Beech has worked in the betting industry for almost 20 years and is an experienced sports betting writer and tipster. He has worked for MailOnline and the Racing Post.