Those searching for value at this year’s Cheltenham Festival might take a punt on Philip Kirby’s outstanding mare Lady Buttons, currently 40-1 for the Champion Chase, and the Ben Pauling-trained Global Citizen, a best-priced 33-1 for the Champion Hurdle on the first day of the four-day bonanza.

If you’re looking for inspiration in backing a longshot this month, then here are five of the biggest shocks to have graced the Cheltenham Festival over the years…

Kirriemuir – 1965 Champion Hurdle

In 1965, the Fulke Walwyn-trained Kirriemuir caused the biggest shock in the Festival’s history when winning the Champion Hurdle at odds of 50-1. Kirriemuir became the second winner of the race for his trainer after Anzio’s success in 1962.

Kirriemuir was up against his stablemate Exhibit A, ridden by Dave Dick, and also faced the Cheltenham specialist Salmon Spray, Nosey and Magic Court.

Exhibit A made all the running in the race and it was only after the last hurdle when Kirriemuir and Willie Robinson asserted their superiority, hitting the front and holding off the fast-finishing challengers Spartan General and Worcran to capture the championship contest.

L’Escargot – 1970 Gold Cup

Owned by Winston Churchill’s cousin Raymond Guest, who was the US ambassador to Ireland, L’Escargot made a return to Cheltenham in 1970 having finished sixth as second favourite behind Persian War in the 1968 Champion Hurdle.

The seven-year-old, trained by Dan Moore, was dismissed in the betting market at 33-1, with Kinloch Brae, running in the famous Arkle silks of Anne Duchess of Westminster, the hot favourite. When Kinloch Brae fell at the third last, the race developed into a match between L’Escargot and French Tan. L’Escargot and Tommy Carberry found more after the last fence to score by a length and a half, with Spanish Steps back in third place.

A year later, L’Escargot successfully defended his Gold Cup crown, this time sent off at 7-2, and in 1975 became the only other horse alongside Golden Miller to win the Gold Cup and Grand National.

Baron Blakeney – 1981 Triumph Hurdle

Trainer Martin Pipe announced his arrival on the big stage with Baron Blakeney’s shock 66-1 victory in the 1981 Triumph Hurdle. Pipe had gained Baron Blakeney for his yard after that horse and Ravens Tower, both owned by Bob Wheatley, had not met their reserves when offered at auction.

Broadsword was the red-hot favourite for the race and hit the front after the final flight, but Baron Blakeney and jockey Paul Leach found a burst of speed up the run-in to deny Broadsword on the line.

Not only was Baron Blakeney Pipe’s first winner at the Festival, he was also the first winner that Pipe sent out at the Gloucestershire track.

Norton’s Coin (centre) stuns Cheltenham with victory in the 1990 Gold Cup – Photo: George Selwyn

Norton’s Coin ­– 1990 Gold Cup

The story of Norton’s Coin’s success in the 1990 Gold Cup for Welsh dairy farmer Sirrell Griffiths is one that stunned the racing nation. Owner-trainer Griffiths only had a couple of horses in his care and one of them was Norton’s Coin, whom he had nurtured from the point-to-point field to compete under rules.

Norton’s Coin had captured a valuable 2m4f chase at Cheltenham the previous April and while Griffiths gave him an entry in the 1990 showpiece, he also intended to enter him in a handicap chase at that year’s Festival. However, Griffiths later discovered that he had missed that deadline for the handicap and there was no other option but to run Norton’s Coin in the blue riband.

Popular grey Desert Orchid was the star act in the Gold Cup field, looking to defend his title, on ground officially described as good to firm. Desert Orchid, as usual, set off at the head of affairs, soon joined by Ten Of Spades. Graham McCourt had Norton’s Coin popping away in midfield and the pair were still travelling well behind the leaders turning for home. As ‘Dessie’ faded, Toby Tobias jumped the last fence in front, only for Norton’s Coin to surge past on the run-in to score by three-quarters of a length at an SP of 100-1.

Cool Dawn – 1998 Gold Cup

Bought by trainer Robert Alner for Dido Harding to ride in point-to-points and hunter chases, Cool Dawn had form at the Festival, having finished second in the 1996 Foxhunter Chase when Harding was the gelding’s jockey.

Returning from a season off because of a tendon injury, Alner suggested to Harding that a professional should ride him. So began the partnership between Cool Dawn and Andrew Thornton. The pair went on to win three consecutive races at Ascot before being pulled up in the Diamond Chase at Sandown a month or so before the 1998 Cheltenham Festival.

A six-week break gave plenty of time for Cool Dawn to recover from a trapped nerve in his shoulder and he started the Gold Cup at 25-1, despite being relatively unexposed. Cool Dawn made all the running in the 3m2f contest and repelled the late charge of Strong Promise to seal a memorable success for all involved.