10 Most Famous (and Infamous) Sports Bets of All Time

There’s something innately thrilling about a bet. The element of risk, the promise of reward, it all adds up to a heart-pounding adventure that’s hard to resist. Especially when we’re talking about sports betting, a realm where unpredictability reigns supreme. But the question that has long stoked the curiosities of many is – which sport is the safest to bet on?

Well, the word ‘safe’ is a bit tricky in this context. Betting, by nature, involves a level of risk. Yet, some sports do have a reputation for being a bit more predictable. Or shall we say, less volatile than others. The crucial thing to consider here is the level of information you have about a sport. And its teams or players. Greater insight leads to more informed decisions, thus enhancing your chances of winning the bet.

Take, for instance, the game of tennis. With fewer variables at play and the match depending largely on the performance of two individuals, many see it as a safe bet. Football, due to its popularity worldwide, offers an abundance of statistical data, making it a favorite for many seasoned bettors. Similarly, horse racing, though a tad more unpredictable, is a sport where you can make informed decisions based on factors like track conditions, horse pedigree, jockey expertise, and more.

But even with all the stats, figures, and insights, betting can sometimes take a wild, unexpected turn. Case in point, the famous sports bets we’re about to explore. These aren’t just instances where someone wagered a substantial amount on an underdog or predicted an unlikely outcome. These are bets that have etched their place in the annals of sporting history. So, sit tight as we delve into these tales of chance, each more intriguing than the last.

10 – Frankie Dettori’s Magnificent Seven

On 28 September 1996, Frankie Dettori had one of the most remarkable days in British racing history, landing all seven winners on the card at Royal Ascot. The odds of such an incredible feat being pulled off were 25,000-1, enough to put off most punters. Dettori himself summed up his own view of his rides’ chances that day before the first when he said, “I could have an each-way chance in the first, and I may win the third.”

This didn’t deter Darren Yeats, who took a punt on Dettori defying the astronomical odds and bet £59 on him landing the card. When Fujiyama Crest, the last of the great Italian’s seven winners for the day passed the post first at odds of 2-1. Yeats walked away with an astonishing £550,000. Even more remarkable given the fact that he had to make the wager in secret. He had promised his wife he would stop betting on Dettori!

09 – Dreaming of Xabi Alonso

We all have dreams, but few of them are as profitable as the one Adrian Hayward had one night about Liverpool midfielder Xabi Alonso.

In 2006, Hayward dreamed that the former Spanish international Alonso had scored a goal from within his own half. So convinced was Hayward that his dream would come true that he placed a bet of £200 on Alonso achieving the unusual feat at some stage during the season at odds of 125-1 with PaddyPower.

When Liverpool took on second division Luton Town in their third round FA Cup tie at Kenilworth Road, Liverpool led 4-3 in stoppage time when the hosts were awarded a corner. The Luton Town goalkeeper went forward into the Liverpool box. And so when the ball broke for Alonso in his half, the net was unguarded. The Spaniard’s long left-foot shot bounced about 30 metres from the goal and rolled in, and the remarkable shot netted Adrian Hayward £25,000.

08 – Never Bet Against Mali

In one of world football’s most remarkable comebacks, Mali were 0-4 down against Angola in the 2010 African Cup of Nations with only 11 minutes of the match remaining. For some reason only known to him, one punter decided to take up the odds of 1000-1 on Mali being able to secure a draw, and put down a £5 bet.

In a truly astonishing reversal, Angola conceded two late goals make it 2-4 as the game entered extra time. The comeback was complete when Mali scored another two in injury time, and the match ended 4-4. The brave punter who took on the bet walked away £5,000 richer.

On the other side of the coin, there is the story of Big Matt, a 19 year old student who, equally inexplicably, punted £4,400 on Angola going on to win the match when it was up 0-4. Big Matt took the punt — despite the potential return being only £44 on his investment. And then watched on in horror as his student loan disappeared into the bookie’s pocket.

07 – A Champion in the Making

All punters like to think that they are pretty good readers of form and can spot a potential winner early on. But few have done this better than Richard Hopkins.

Hopkins saw future F1 World Champion Lewis Hamilton racing go-karts in 1998 when he was just 13 years old. And so convinced was he by the Briton’s precocious talent that he placed a £100 bet at odds of 500-1 on Hamilton winning the F1 crown before he reached the age of 25. Hopkins showed his faith in Hamilton becoming a superstar with another £200 bet at odds of 200-1 that he would win his first Grand Prix by the age of 23. He then doubled down with a further bet of £50 at odds of 1500-1 that both of his other wagers would come in.

All up, when Hamilton won the F1 Championship in 2008 aged 23 (after winning his first Grand Prix in Canada in 2007), Richard Hopkins’ belief in the young driver’s ability had earned him an astonishing £165,000.

06 – The Win Was on the Cards

All sports fans like to show faith in their teams, but an anonymous St Louis Cardinals fan took his to another level in 2011.

Five games back from a Wild Card spot on 12 September, the Cards’ fan took a $250 punt on their reaching the World Series at odds of 500-1. He then took it one step further, with another $250 bet on Tony La Russa’s team actually going on to win the Championship, this time at odds of 999-1.

In one of baseball’s most remarkable runs of form, the Cardinals suddenly turned it around, finishing second in the NL Central behind Milwaukee and taking the Wild Card spot by a game over the Braves. They then went on the beat Philadelphia in the Divisional Series, the Brewers for the NL Pennant. And then upset the Texas Rangers 4-3 to take the World Series.

The punter who showed such faith back in September was duly rewarded, and walked away with pay outs totaling $375,000.

Famous Sports Bets
Sports Betting

05 – Mick Owes it all to Kahn

The name Mick Gibbs is synonymous with huge sporting bet wins. In 2001, the Staffordshire roofer bet 30p on a 15 fold football accumulator that eventually netted him £500,000, after all 15 legs came in at combined odds of 1,666,666-1.

The story has added spice in the fact that after the first 14 legs came in, Gibbs’ potential fortune was resting on the 2001 Champions League Final between Bayern Munich and Valencia — a match which famously went to a nerve-wracking penalty shoot out. However, when Man of the Match Oliver Kahn saved Mauricio Pellegrino’s seventh spot kick, Gibbs had successfully pulled off an amazing betting coup.

What is even more incredible about this story is that this was not Gibbs’ first huge accumulator win — in 1999, he landed a £157,000 payout on a £2.50 9 fold football acca.

04 – The Leicester City Fairytale

Leicester City’s triumph in winning the English Premier League in the 2015/16 season against all odds has become the stuff of sporting legend. There were also some great betting triumphs that accompanied it. Along with some severe pain for the bookmakers, with their combined losses estimated to be in the region of £25 million.

At the start of the season, the Foxes were quoted at odds of 5000-1 outsiders to win a first ever Championship in their 132-year history. Their manager, the affable Italian Claudio Ranieri, was expected to not even last the season. And was the bookie’s favourite to be the first Premier League boss to get the sack.

However, some incredibly optimistic City fans took a punt despite the astronomical odds. Ladbrokes took 57 bets at 5000-1, although 36 punters weren’t able to hold their nerve and took early pay outs. However, the 21 loyal fans who kept the faith were duly rewarded, with one City supporter taking the bookmaker for £100,000 on his £20 bet.

As well as the triumphs, there were a few new misses as well. A man in Warwickshire cashed out his £50 bet a few weeks before the season ended and took an early pay out of £72,000 — had he stayed on board, he would have netted £178,000.

03 – England Defy the Odds

England’s win in the Ashes Test against Australia at Headingley in 1981 remains one of the sport’s most amazing comebacks. However, the match has passed into legend not only because of the players’ exploits on the field. But off it as well.

The hosts were being thoroughly outplayed and seemed to have no hope of recovering in the match. The bookmakers agreed and were offering odds of 500-1 on an England victory. Such lavish odds prove too much for Australia’s legendary fast bowler Dennis Lillee and wicketkeeper Rod Marsh, who for fun place bets of £10 and £5 respectively on their not being able to get the job done and Australia losing the match.

Up until this game, no team in Test Match cricket had come back from England’s position of being required to follow on and win a match since 1894. It looked an impossible task. Until Ian Botham’s swashbuckling innings of 149 not out, followed by Bob Willis’ blistering spell of pace bowling in which he took 8 wickets, saw England home for a remarkable 18 run win.

However, the bets of Lillee and Marsh soon became the focus. Did the £7,500 that they stood to win if England got up affect their performances? Both players have always vigorously denied it, as have other players on that fateful day. But there is no doubt that, given the people involved and the seemingly impossible outcome. This remains one of the most controversial sporting bets of all time.

02 – Cricket’s Darkest Day

Betting on cricket was again in the spotlight in 2010, when England played Pakistan at Lord’s. As a result of investigations that had begun before the match, the Pakistan captain Salman Butt, along with bowlers Mohammad Asif and Mohammad Amir, were found guilty of what is known as spot-fixing. In this case arranging to bowl no-balls on a particular delivery during a specified over, in return for payments from a bookmaker.

Mazhar Majeed, the agent at the centre of the scandal, was caught in an undercover sting operation telling reporters that Amir would bowl a no-ball on the fist delivery of the third over. And that Asif would also bowl a no-ball on the sixth delivery of the tenth over. Both events duly occurred, and the fix was in.

However, the scam was eventually uncovered. And Butt was sentenced to 30 months in prison. Asif and Amir received sentences of 1 year and 6 months respectively. The cricket careers of Butt and Asia were ended by the scandal. Although Mohammed Amir returned to playing international cricket in 2016 after serving a five-year ban imposed by the ICC.

01 – Father Knows Best

Most fathers of sporting prodigies have great faith in their offspring’s abilities. But Gerry McIlroy, father of the 2014 British Open winner Rory McIlroy, genuinely put his money where his mouth is.

In 2004, when Rory was 15, his father put a £200 bet on the up-and-coming star winning the British Open within ten years at odds of 500-1. Several friends of the family also took advantage of the generous odds. They too had seen at first hand the Northern Irish youngster’s abilities.

When Rory McIlroy won the Open at Royal Liverpool in 2014 by two strokes, dad Gerry’s joy was compounded by his picking up £100,000 from the bet made with Ladbrokes ten years earlier. Additionally, the friends who showed similar faith pocketed £80,000.

Ladbrokes says that it takes around 300 similar bets each year from optimistic parents and supporters. Although it’s rare that they come off in the way that this one did for the McIlroy family.

The Most Profitable Sports to Bet On

Stepping away from our intriguing collection of bets, let’s take a moment to consider another equally exciting question. What kinds of sports are the most profitable to bet on? Now, it’s essential to understand that profitability in betting doesn’t solely hinge on the sport you choose. It’s a medley of numerous factors including your understanding of the sport, your ability to analyze odds, the timing of your bet. And yes, sometimes, just pure, dumb luck.

However, statistics do point out certain sports that yield higher profits. Football, with its global appeal and plentiful data, allows for many types of bets, thereby increasing your chances of winning. Horse racing, despite its unpredictability, remains profitable due to the higher odds it offers. Tennis and basketball also come highly recommended for their easy-to-understand betting structures.

But remember, while the thrill of winning can be intoxicating, it’s essential to maintain a balanced approach. Betting, if not managed responsibly, can lead to a gambling problem. So, whether you’re taking inspiration from these audacious bets or considering taking a plunge into the betting world yourself. Always remember to gamble responsibly and enjoy the process rather than solely focusing on the outcome.

In the world of sports betting, the unexpected is the norm. And these famous bets are a testament to that fact. From rags-to-riches stories to heartbreaking losses, they highlight the many faces of this thrilling domain. One where fortunes are made or lost on the flick of a ball or a horse’s sprint.