If you Google ‘Famous Five’, you’ll be introduced to Julian, Dick, Anne, George and Timmy the dog or, in other words, the characters created by Enid Blyton in her collection of adventure stories for children. However, if you add the word ‘Dickinson’ to your search criteria when you’re looking up racing questions, you will discover not fictional tales of twee postwar Englishness, but rather a factual account of an altogether different ‘Famous Five’.

The ‘Dickinson’ in question is, of course, Michael W. Dickinson who, in 1983, pulled off the most remarkable training feat in the history of horse racing by saddling the first five finishers in the Cheltenham Gold Cup. Dickinson had already achieved a notable 1-2 in the premier steeplechase with Silver Buck and Bregawn in 1982 and those two were among his five runners – the equivalent of 9% of all the horses in his yard at Dunkeswick, near Harewood, Yorkshire – who lined up for the 1983 renewal.

For the record, those horses were, in finishing order, Bregawn (10/3 favourite), ridden by Graham Bradley, Captain John (11/1), ridden by David Goulding, Wayward Lad (6/1), ridden by Jonjo O’Neill, Silver Buck (5/1), ridden by Robert Earnshaw and Ashley House (12/1), ridden by Dermot Browne. Bregawn made all the running to beat Captain John by 5 lengths, with Wayward Lad a further 1½ lengths behind and a distance back to the other pair. Amateur jockey Dermot Browne, later a trainer, was subsequently ‘warned off’ for 10 years in 1992, and for a further 20 years in 2002, after admitting doping horses.

How much the Cheltenham Gold Cup is worth really depends on whether we’re talking about the value of the prize money on offer or the value of the physical trophy – that is, the Gold Cup itself – presented to the winning owner. In the case of the former, the answer is straightforward; in 2019, the Cheltenham Gold Cup offered £625,000 in prize money, just over £350,000 of which was awarded to connections of the winner, Al Boum Photo.

However, in the case of the latter, the answer requires some educated guesswork regarding the monetary value of the Cheltenham Gold Cup trophy and an appreciation of the historical context in which it is presented. In 2018, Cheltenham Racecourse was reunited with the original Gold Cup trophy, first won by Red Splash in 1924, which was mounted on a plinth bearing the names of all the previous winners and, since 2019, has been presented to the winner as a perpetual trophy.

The Cheltenham Gold Cup trophy reportedly consists of 644g, or approximately 1lb 7oz, of nine carat gold – which even at current scrap gold prices is worth over £7,000 – plated in 18 carat gold to give it its rich, lustrous colour. Of course, the Cheltenham Gold Cup trophy is unique and irreplaceable – the winner owner receives a replica to keep, while the original remains at Cheltenham Racecourse throughout the year – so effectively priceless from an historical and cultural perspective.

At just under 16 hands high, Tiger Roll is small for a steeplechaser and was, in fact, originally bought by owner Michael O’Leary to win the Fred Winter Juvenile Handicap Hurdle at the Cheltenham Festival. However, Tiger Roll proved significantly better than anticipated, winning the Grade One Triumph Hurdle, on just his second start for his new connections, in 2014.

Subsequently, despite his diminutive size, fences have been the making of him. Of course, in April, 2019, he made history by becoming the first horse since Red Rum, in 1974, to win the Grand National two years running, but he also has three further successes at the Cheltenham Festival to his name. He won the National Hunt Chase in 2017 and the Glenfarclas Cross Country Chase two years running, in 2018 and 2019, en route to victory in the Grand National.

Still only a nine-year-old, Tiger Roll takes the odd liberty with an obstacle but, although he did once unseat his rider in a novices’ chase at Galway, when bumped by a rival at the second-last fence, he has never fallen. So, while Michael O’Leary has said that Tiger Roll is ‘very unlikely’ to run in the Grand National in 2020, another win in the Glenfarclas Cross Country Chase – which would be his fifth at the Cheltenham Festival – looks within the realms of possibility.