4 Unforgettable Cheltenham Festival Betting Gambles

4 Unforgettable Cheltenham Festival Betting Gambles
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Given the strength of the Cheltenham betting ring each March, and the importance of the Festival for the off-course betting industry too, the meeting has always had a reputation as the cradle of the old-fashioned betting coup.

But there are a variety of ways in which the bookmakers can find themselves skewered, or occasionally, let off the hook.

Listing Cheltenham's gambles by the size of the recorded bets is one way to categorise the scale of the punt, and certainly better than being told by bookie press office that 'this favourite has cost the industry a random multiple of £1m'.

Some of these Cheltenham gambles have been spread across the betting and horse racing industries, often as affairs carefully orchestrated by shrewd connections.

Some of the biggest plunges have been very private affairs, where intrepid backer and fearless layer clash, but just as often, the public latches on to a well-hyped runner, or runners, and the liabilities spiral.

Below you'll find just some of such stories in the history of gambling at the Cheltenham Festival, with endings of contrasting fortune.




1991 - Noel Furlong, Destriero & The Illiad

Noel Furlong's Destriero lands Cheltenham betting gamble in 1991 Supreme Novices' Hurdle at Festival

There are many layers to the famous story of owner Noel Furlong’s successful tilt at the betting ring in 1991 when Destriero beat future Champion Hurdle winner Granville Again in the Supreme Novices' Hurdle.

At its simplest, it’s the story of a man who knew he had a hugely talented horse, but one who had won just a maiden hurdle, and was running in the hottest novice hurdle at the biggest meeting of the year - when racing bookies were waiting with gaping satchels to take the cash.

That explains how Furlong managed to back his charge, running in the colours of wife Betty (who was also intended to be the trainer, but was refused a licence, with Andy Geraghty taking the official role) to win a reputed £1.5million, without his odds going through the floor.

Furlong Wanted On Customs Charges

In fact, Destriero drifted from 5/1 to 6/1 on-course, as the public failed to follow the signs. In fairness, they could be forgiven for missing the biggest sign, that being the very presence of Noel Furlong in Britain, where he had been a wanted man for some time, due to a misunderstanding with Her Majesty’s Customs and Excise.

In order to avoid arrest, the gambler had to pay a reported debt of around £500k. Any man willing to pay a cool half million for his ticket to the races must have something worth cheering.

Furlong, a revered poker player, was often flush, and his willingness to pay off the customs men was aided by a couple of successful wagers at Leopardstown either side of the New Year.

Destriero won his maiden hurdle at Leopardstown’s Christmas meeting and the 2/1 SP was generous, but the money landed there was nothing to what was won when The Illiad won the Ladbrokes Hurdle in January, with his owner backing him initially at 33/1 and then down to 7/1 on the morning of the race.

One Gamble Became Two

That gave him his ante for the Cheltenham bet, and some more besides, so Furlong had another idea, entering The Illiad, a useful if unsound handicapper, in the Champion Hurdle, where he had the look of a rank outsider.

Details of how much money was running on to The Illiad after Destriero won the opening race on that famous Tuesday vary with the telling, but the fact that the patently overmatched The Illiad was sent off at 11/2 for the Champion Hurdle shows the extent of the panic which had set in among rails and boards bookmakers, with the off-course firms now facing enormous liabilities.

In the end, The Illiad failed to beat another horse in a race won by Morley Street, but Furlong had landed the touch he wanted, and probably got as much satisfaction seeing the Cheltenham betting ring in pandemonium at the prospect of finding another few million for his audacious double attempt.


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1982 – Danno & Mick Heaslip and For Auction


Not all Cheltenham gambles leave the bookies in tears and prices crashing through the floor.

One of the most celebrated punts of the last 40 years, is memorable not for the amount won (although it was no small change), but the joie de vivre of the occasion and the sense of living the dream.

When the Michael Cunningham-trained For Auction won the 1982 Champion Hurdle for the Heaslips, stalwarts of the Galway rugby community, the result was a shock for most, as an SP of 40/1 would indicate, but not for Mick Heaslip.

300 Bottles Of Champagne

He had backed For Auction ante-post at that price, while Danno Heaslip availed himself of the 50/1 readily available on the track. Before leaving the Golden Valley Hotel on the morning of the race, Danno had told the hotel manager to have 300 bottles of champagne ready for the party they had planned for the evening, so he thought he’d better have a small bet to cover that expense.

The idea of losing was not considered, and when For Auction bounded up the hill ahead of the fancied pair of Broadsword and Ekbalco, the corks started popping. Keen to party in traditional style back at the hotel that evening, this entire venture is summed up by the conversation Danno had with the manager as he surveyed the downstairs bar:

“Can we get a piano in here?”

“I’m afraid we don’t have a piano, sir.”

“Well then, you’d better buy one!”




1986 – Terry Ramsden and Brunico

When Dawn Run started 15/8 for the 1986 Cheltenham Gold Cup, there were many who believed she was a terribly short price, given she was effectively a novice, and had unseated her rider on her previous visit to Cheltenham in January.

History shows that she snatched victory from the jaws of defeat to smash the race record (just as she had in the Champion Hurdle in 1984) and justify that short price, but what would the SP have been if Brunico had won the Triumph Hurdle?

There seems no obvious connection between the two, but knowing who owned Brunico might point you in the right direction.

Terry Ramsden, stockbroker, wide-boy, inveterate gambler, was at the height of his fame in the mid-80s, and was making a splash not only as a fearless punter, but a high-profile owner.

£1million Bet Only Hors D'Ouevre

On the middle day of the Cheltenham Festival, Motivator had won the Coral Golden Hurdle, landing bets in the region of £1million for Ramsden, but he had bigger fish to fry and he had been backing his own horse, Brunico, in doubles with Dawn Run for some time before the pair lined up for their respective races on that fateful Thursday.

To know how close he came to landing a Cheltenham Festival coup, which was at least as big as Noel Furlong’s attempted double above, you just have to watch the 1986 Triumph Hurdle.



Starting at 16/1, Brunico was held up by Dermot Browne, and going well enough until he made an error at the fourth hurdle, costing him momentum and ground. By the time jockey Peter Scudamore kicked Solar Cloud for home at the penultimate flight, he was at least 10 places, and some thirty lengths clear of the distinctive grey in Ramsden’s bright blue and white hoops.

The cause looked hopeless, and it didn’t seem much more promising at the last, despite Brunico moving into a share of fourth, Solar Cloud and Son of Ivor still a dozen or more lengths ahead.

That Brunico managed to split the pair, finishing a close second, shows just how fast he was finishing and 50 yards past the post he was on his in front, on his own. Alas, it was too late, in more ways than one.

Death Of All Ramsden Gambling

While Ramsden was lauded at the time for his success, it transpired that even with his well-publicised wins, he was haemorrhaging cash, reportedly losing £25million in the 1985/86 season alone.

If Thursday, March 13th, 1986 was a dark day for Ramsden, worse was to follow in October 1987 when the Black Monday stock market crash saw the collapse of his business and with it the means to fund his compulsive gambling; the coup de grâce came when Ladbrokes, who had seen enormous financial benefit from his profligacy, had him warned off for the non-payment of his outstanding debt to the firm.


1998 – Martin Pipe & A P McCoy – A Nationwide Gamble

Martin Pipe and A P McCoy landed multiple gambles at 1998 Cheltenham Festival

The 1998 Cheltenham Festival is one I remember vividly, as I had recently taken over a small branch of Ladbrokes in Notting Hill Gate, and was keen to prove my worth as a betting shop manager, with growing the profits of the shop the primary aim.

That week in March is indelibly etched in my memory as one which threatened to throw a spanner in the works, with two men to blame - trainer Martin Pipe and jockey Tony McCoy.

There was plenty of cash flying around, with turnover helped by a team of builders on a nearby job adding to the usual clientele, but results didn’t go our way. The builders, and countless others around the country had a simple method for betting on Cheltenham - trust Martin Pipe and Tony McCoy, and the pair kept delivering.

Unsinkable Partnership Pays Gambles Galore

Champleve in the Arkle Novices' Chase saw the payout busy, but not so busy as after Unsinkable Boxer’s win in the finale, and after a couple of near misses with Torboy and Or Royal on day two, normal service resumed with a bang.

McCoy finished the meeting in the best possible style, winning the last three races on board well-backed favourites, with Blowing Wind’s SP of 15/8 in the County Hurdle - the traditional getting-out stakes - telling its own tale.

Champleve, and Cathcart Chase winner Cyfor Malta were owned by a big-hitting punter, the late David Johnson, but the damage done to bookmakers up and down the country that week was inflicted by ordinary punters, who had latched on to a winning Cheltenham Festival betting formula.

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