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The 1990 renewal of the Cheltenham Gold Cup was supposed to be all about the popular grey Desert Orchid, who had enjoyed arguably his finest hour when getting the better of an epic duel with Yahoo in the ‘Blue Riband’ event in 1989. Although now an eleven-year-old, back on his favoured fast ground Desert Orchid was again sent off favourite, at 10/11, to defend his title.

Ridden by Richard Dunwoody, who had replaced Simon Sherwood as his regular partner, Desert Orchid made most of the running, as he had done the previous year. However, although he held every chance at the second-last fence, ‘Dessie’, as he was popularly known, could find no extra in the closing stages and eventually finished a respectable third, beaten 4¾ lengths.

Victory went to the completely unconsidered 100/1 outsider Norton’s Coin, a nine-year-old bred, owned and trained by Sirrell Griffiths, a permit-holder and dairy farmer from Nantgaredig in Carmarthenshire, West Wales. Remarkably, Griffiths had just three horses in his charge and considered training his ‘hobby’. Reflecting on his extraordinary success some years later, he said, ‘I never had any ambitions and was quite happy just working with the horses at home and having the odd runner in a race.’

Indeed, Norton’s Coin was only entered in the Cheltenham Gold Cup as an afterthought, with Griffiths originally preferring an entry in one of the handicap chases, in which he felt the horse was nicely weighted. However, he missed the deadline for his preferred entry, so he was forced to part with £1,000 for a Gold Cup entry, seeking to finish in the first six to cover his costs.

Victory for Norton’s Coin was undoubtedly a major shock, but there appeared no fluke about it. Ridden by Graham McCourt, the gelding was always travelling well and, although ultimately all out to hold Toby Tobias by three-quarters of a length, broke the course record in the process.

The 2014 renewal of the Cheltenham Gold Cup featured thirteen runners, including the reigning champion, Bobs Worth, and Silviniaco Conti, who had fallen, when travelling well in third place, at the third-last fence in 2013. The pair started 6/4 favourite and 11/4 second favourite, respectively, but while both were involved in an ‘eventful’ finish to the race, neither finished in the first three.

Victory went to the eight-year-old Lord Windermere, in controversial circumstances. The winner, who prevailed by just a short head and three-quarters of a length, had to survive a fifteen-minute stewards’ inquiry before the result was confirmed. Lord Windermere was found to have interfered with the eventual second, On His Own, and the eventual third, The Giant Bolster, but the interference was deemed ‘minor’ and he was given the benefit of the doubt.

Trained by Jim Culloty and ridden by Davy Russell, Lord Windermere had won the RSA Insurance Novices’ Chase at the Cheltenham Festival in 2013, but was a largely unconsidered 20/1 chance in the Cheltenham Gold Cup as a result of some indifferent form since. Indeed, his victory owed much to the perseverance of his jockey, who later admitted that he was tempted to pull up on the first circuit after receiving little encouragement from his mount.

In any event, Lord Windermere was detached at the rear of the field just before halfway, but made headway under pressure from the second-last fence and, despite hanging badly right close home, won by a short head, all out. Culloty, probably better known as the jockey of three-time Gold Cup winner Best Mate, joined Danny Morgan, Pat Taaffe, Fred Winter and Jonjo O’Neill as one of just five men to have ridden and trained a Cheltenham Gold Cup winner.