Many dyed-in-the-wool punters spend hours poring over the formbook in an effort to win a life-changing sum of money but, ironically, the punter who won the largest winning dividend in the history of the Tote Jackpot was, by his own admission, ‘not a horse racing man’. The punter in question was, in fact, Steve Whiteley, a 61-year-old heating engineer from North Tawton, North Devon, who was not a regular racegoer and attended a meeting at Exeter Racecourse, in March 2011, as part of a free promotion.

Having scrapped his original, permed Tote Jackpot entry, Whiteley settled, instead, for a single line entry, costing just £2. Nevertheless, he correctly predicted the first four winners – Semi Colon at 2/1, Black Phantom at 12/1, Ammunition at 16/1 and Mr. Bennett at 16/1 – and, by that stage, just seven entries remained. His fifth selection, Lundy Sky, at 5/1, also won at the expense of odds-on favourite Glitzy D’Ocala leaving his the only ticket remaining in the Tote Jackpot.

His sixth, and final, selection, Lupita, was on a losing run of twenty-eight and was ridden by Jessica Lodge, an amateur rider who had yet to ride a winner under National Hunt rules. Whiteley said afterwards that ‘Lodge is just a name that sticks in my head’. Perhaps understandably, Lupita was sent off 12/1 joint-seventh choice of the thirteen runners, but belied those odds by keeping on gamely to lead inside the last hundred yards and lift the spoils by three-quarters of a length. In so doing, the seven-year-old won an incredulous Whiteley £1,445,671.

Apparently, ‘If at first you don’t succeed, try, try again’ was originally a maxim used to encourage American schoolchildren to do their homework. However, the importance of not giving up too easily was highlighted by an anonymous Coral punter who, in April, 2017, staked £19 on a permed accumulator bet and won £822,972.75 or, in other words, the highest horse racing payout the bookmaking firm has made since it was established in 1926.

The unidentified man, believed to be from Leicester, made five selections at the home of Irish jump racing, Punchestown, in Co. Kildare, and combined them in five £3 four-folds and one £4 five-fold. Das Mooser, about whom he had taken 10/1, set the ball rolling when making all to win the hunter chase, on his debut under National Hunt rules, at half those odds and was followed, in quick succession, by Woodland Opera, at 9/2, in the novice chase and Definite Ruby, at 7/1, in the mares’ handicap chase. Just over an hour later, Bacardys, at 10/1, beat favourite Finian’s Oscar by a short head to win the Tattersalls Ireland Champion Novice Hurdle and, later in the evening, Canardier – backed at 33/1, but sent off at just 8/1 – completed the clean sweep by winning the flat race.

Not that our intrepid punter was aware of any of the goings-on at Punchestown, having headed off for a night out. However, he did eventually check the racing results in the early hours of the following morning and later described his life-changing win as ‘the realisation of a lifetime dream’. Apparently, the man, who is the son of a bookmaker, had been placing similar bets, in the form of trebles and accumulators, on a daily basis for the previous twenty years but, in his own words, ‘kept hitting the woodwork’.

Even back in 2008, fifty pence was less than the price of a loaf of bread, or a pint of milk, but that was the amount staked by Fred Craggs, a fertiliser salesman from Thirsk, North Yorkshire, who would subsequently become the first ‘betting shop millionaire’. The day before his sixtieth birthday, in February, 2008, Craggs placed an eight-fold accumulator on horse races at Sandown Park, Nad Al Sheba, Warwick and Wolverhampton at his local William Hill betting shop. Fittingly, under the floodlights at Gosforth Park that evening, his eighth and final selection, A Dream Come True, won at 2/1 to land cumulative odds of nearly 2,800,000/1.

Craggs remained blissfully unaware of his good fortune until the following day, when he visited another William Hill betting shop in nearby Bedale. Having placed another five bets, each worth fifty pence, as was his custom, he asked staff to check his betting slip from the previous day. Craggs apparently visibly paled when informed that his total winnings were exactly £1,000,000 – subject to maximum payout rules, but nonetheless unprecedented in the history of British betting shops – but later said that he had experienced only a ‘dull sensation of excitement about the win’. William Hill spokesman David Hood was, thankfully, a little more upbeat, saying, ‘It is a staggering bet, and earns him a place in history as the world’s first betting shop millionaire. Even a scriptwriter couldn’t have dreamt this one up.’