The Craziest Longshot Bets That Won


Surprised man checking phone

In December 1989, a brave/crazy/psychic chap in Wales went into a betting shop and staked £30 that by the year 2020 Cliff Richard would be knighted by the queen, Eastenders would still be on tv, Aussie soaps, Neighbours and Home and Away, would also be on tv and that the band U2 would still be together.

His odds on these mammoth (and totally random) predictions were a very tidy 6479/1, meaning that he pocketed just short of £200k. What went through his mind when making these completely off the wall and unrelated predictions is unknown, but he certainly isn’t the only punter who fancied the outsider. Here we take a look at some more of the bonkers bets that defied the odds and won!

Greece to be European Champions at 150/1

Beating Spain to the top spot in their Euro 2004 qualifying group was no mean feat in itself, but bookies and pundits alike paid no heed to Greece’s accomplishments and ranked them firm outsiders at 150/1 to lift the trophy.

With a host of top teams all with some world class talent in their squads no one would have thought that the nation with a population only just over 10 million would have stood a chance against some of the greatest names in European football. Prior to the tournament they had only ever qualified for one World Cup and had failed to win a game at their only previous Euros appearance. Those odds of 150/1 were perhaps understandable, despite their fine showing in qualification.

Spain had the lethal finishers Raul and Fernando Morientes, France had the silky skills of Thierry Henry and the defensive rock Desailly, Portugal had home advantage and a certain Cristiano Ronaldo. Even England had an amazing team on paper with Steven Gerrard, Frank Lampard, Paul Scholes, David Beckham, Michael Owen et al, whilst Germany and Netherlands were also very strong.

This should have been a show of some of the most exciting football on the planet, but the Greek team was built around containment, not letting the other guys score at any cost with the hope of nicking a goal at the other end on the break. It wasn’t beautiful but it certainly was effective.

Hosts Portugal were the final hurdle for this plucky Greek team. Even having made the final, Otto Rehhagel’s outfit were priced at 10-1 to lift the trophy. Unfortunately for Portuguese fans games are won on the pitch, not at the bookies and Ronaldo and co just couldn’t break through the Greek defence.

Greece’s against the odds success reportedly netted one lucky punter in Surrey a whopping £332,000 thanks to several bets throughout the tournament. Were you on the Greeks at 150/1?

Buster Douglas to Beat Mike Tyson at 42/1

Ok, so maybe the odds on this one aren’t particularly large compared to some others on this list. But when you think that a boxing match is essentially a two-horse race, albeit one that has three outcomes, then it just goes to show how unfavoured this guy really was.

With Tyson unbeaten in his previous 27 bouts, and Douglas only ranked seventh at the time, this was seen as just a “warm up” fight for Tyson before he took on fellow heavyweight top dog Evander Holyfield.

Once the fight started however it became apparent that this was not going to be an easy victory for Tyson. In his previous fight Mike Tyson had knocked out Carl Williams in 93 seconds but Buster Douglas wasn’t about to let the same happen to him.

As the fight wore on into the middle rounds both fighters were pretty evenly matched although Iron Mike was certainly on top. Tyson however had a problem, with his eye swelling up, leaving him struggling to see the incoming punches. Amazingly this wasn’t helped by the fact that his corner team, so confident of a quick win, hadn’t even bothered to take any ice packs to the fight!

Then in the 10th round the unthinkable happened and the underdog had his day! Having been knocked down in the dying seconds of the 8th, those betting on Douglas must have feared the worst. But he came back with a solid 9th round and then followed that up with a left uppercut that knocked Tyson to the canvas and ended his unbeaten record. Douglas had done the unthinkable and was crowned the new heavyweight champion of the world!

It is reported that one punter risked $168,000 on Tyson hoping to “steal” just $4,000 on what he thought was definitely going to win. On the other hand, Vegas oddsmaker Jimmy Vaccaro told of a bet of $1,500 at 37/1 on Douglas. That’s an easy $55,500 profit!

Liverpool to Play Spurs in the Champions League Final at 65/1

In more recent times we have also seen crazy bets, crazy both for their odds and their seemingly random nature. Although a European cup tie is a two leg affair, it certainly looked like both Liverpool and Spurs were out of the competition in 2019 after only the first legs of the semi finals.

Liverpool were 3-0 down, suffering an embarrassing defeat to Spanish giants Barcelona, and needed a four-goal winning margin against the Catalans in the return leg, and to top it off they were without two of their key men up front. It was a seemingly impossible task. Especially so if the likes of Lionel Messi and co were to grab an away goal leaving the Reds searching for five!

Spurs looked a little more likely to progress after the first leg, trailing by only a goal, albeit that having to play the second leg away made their task much harder. But worse was yet to come, as an early Ajax goal in the second leg, followed by another 10 minutes before half time, left Spurs needing to find three goals in the ensuing 45 minutes.

But football is certainly not one for the fainthearted, Divock Origi, standing in for the injured Mo Salah, scored a brace either side of a Gini Wijnaldum double, to secure Liverpool’s passage to the final. Over to you Tottenham …

Mauricio Pochettino’s men weren’t to be outdone for drama however, as Lucas Moura scored a second-half hat-trick, including a goal in the sixth minute of injury time, to ensure that both European competitions would have an all-English final for the first time ever.

Prior to the second legs the odds of Liverpool and Spurs meeting in the final were a massive 65/1 but that didn’t stop a number of hopeful fans – or we can call them crazy if you prefer – backing two stunning fightbacks.

Olympic Wrestling: Rulon Gardner Upsets Odds of 2000/1

Aleksandr Karelin, or the Russian Bear as he was otherwise known, hadn’t lost a wrestling match in 13 years and his career record stood at 887 wins and only 1 loss. So it was no surprise then that he was the odds-on favourite to retain his gold medal at the Sydney Olympics in the year 2000.

Rulon Gardner on the other hand was a farm labourer who “wrestled” cows for a living, and he had never finished higher than 5th in an international competition. He was therefore priced at seemingly hopeless odds of 2000/1 to take the gold medal at the games.

The final between the pair is still disputed to this day, partly because Karelin had fought two opponents the previous day and was a little jaded, whereas Gardner was afforded significantly more rest and was undoubtedly the fresher of the pair. Also the winning point was scored by a technicality and not by any feat of skill on Gardner’s part.

Once he had the point in the bag Gardner actually chose the tactic of Par Terre, essentially just lying down on the mat and making himself a deadweight so that his opponent couldn’t take the point from him. Not an illegal tactic, but not exactly winning in style either.

Nonetheless, Gardner was able to hold on for the win and secure himself the gold medal, defying all the odds against the greatest wrestler in modern times. Admittedly, Olympic wrestling isn’t the biggest betting sport around but there were certainly some punters who landed this 2000/1 winner!

Leicester City 5000/1 Miracles

No modern article about crazy longshot bets is complete without some mention of Leicester’s miraculous title win in 2016. The Foxes were priced at 5000/1 at the start of the season and absolutely no one would have predicted that Claudio Ranieri’s men would lift the title. Well, as it turns out, several people not only predicted it but backed it!

With the so called “big teams” all going through transition phases or simply having bad seasons. The campaign was open for someone to step up and take charge in the title race. Leicester were that team, and take charge they did. The Foxes certainly made the most of the other teams’ drop in form and played some superb football along the way. Never seeming to look back once they hit top spot they won the league with two games to spare.

All Leicester needed was Chelsea to take points off Tottenham when the two met at Stamford Bridge, and so the celebrations were wild in all the pubs in Leicester as Chelsea managed to come back from a two-goal deficit to hand them the title of Premier league champions for the first time in their history.

Many punters famously backed them at 5000/1 but what really cost the bookies big time was the many bets along the way struck at shorter, but still lengthy odds. Even when the East Midlanders were top of the table most experts expected them to falter but they didn’t, making this footballing miracle happen and making lots of punters very happy.

US Winter Olympics Ice Hockey team – 1000/1 Shots

The “Miracle on Ice”, as it was dubbed after the 1980 Winter Olympic final, was a contest between the Soviet Union, four time gold medallists, and seasoned professionals, and massive 1000/1 underdogs the United States.

The US team was comprised mainly of youngsters used to only playing in college leagues, and had no experience whatsoever at the highest levels of the game so to even reach the medal round was a great achievement. At this time the States didn’t send NHL stars to the Olympics and in a clash with the Soviets before the games they had been thrashed 10-3!

In the now legendary game (there is a film about it!) they soon found themselves behind in the first period, but managed to level, before the Soviets scored again. Against the odds the US youngsters were able to level again in the last second of the period. The first period ended 2:2 but few doubted who would win, even with the underdogs playing on home ice in Lake Placid.

The favourites then replaced their goalkeeper immediately after the equaliser, a move that Soviet manager to this day calls his “greatest mistake”. The backup keeper managed to keep a clean sheet in the second period though, with his team completely outplaying the opposition, but managing only a solitary goal to give them a slender lead going into the third and final period.

Then the States somehow managed to spark into life in the final period, helped by having a power play that they managed to capitalise on and grab the equaliser. Then up popped captain Mike Eruzione with 10 minutes left to play. Having just come onto the ice he slipped a shot past the keeper to give the States their first lead of the match.

The final 10 minutes of the match must have been agony for the home supporters, however they managed to keep “the enemy” out and leave themselves with only one match left to play of the round robin medal phase in order to secure the gold medal, against odds of 1000/1 at the start of the games.

They would go on to claim the gold, coming from 2-1 down in the last period to beat Finland 4-2. The Soviet side took out their anger on Sweden in their final game, winning 9-2, but the damage had been done and they only took home the silver medal. The Miracle on Ice will never be forgotten by US hockey fans and nor will it be forgotten by those crazy punters who backed them at four-digit odds!

St Louis Rams Land Super Bowl at 300/1

The St Louis Rams had a terrible start to the 1999 NFL season, with star quarter back Trent Green suffering a serious knee injury before a ball had even been thrown. The Rams were unheralded to say the least, having finished the 1998 campaign with a record of 4-12 but stand in quarter back Kurt Warner took Green’s place and amazingly led his team to a 13-3 season.

The Rams were widely available at 200/1 in the US but in the UK had been priced at a massive 300/1 following Green’s injury. Having reached the Super Bowl against the Titans, the Rams were made seven-point favourites to lift the trophy. They managed to take a 9-0 lead by halftime but the contest was tight and the game certainly wasn’t over.

They did manage to extend their lead in the third quarter to 16 points and no team had ever come back from such a deficit in the Super Bowl. But that’s exactly what the Titans managed, 16 unanswered points to tie the game with two minutes left on the clock in the final quarter.

The comeback wasn’t to be however, and anyone who had backed the Rams at triple-digit odds would soon be claiming their winnings. It was fitting that Warner still had something to say about the result and the stand-in QB completed a 73 yard touchdown pass which would clinch the game and send punters into delirium. Various Vegas bookies have spoken of the bets they accepted and we can only assume there more such happy punters around the world too.

500/1 England Ashes Win 1981

England got off to a terrible start in the 1981 Ashes, and only needing to tie the series to ensure they retained the urn, they found themselves one nil down after two matches, and being seriously overrun in the third.

A win for Australia in the middle clash at Headingley would leave them only needing a draw in either of the last two matches to wrest the urn back from the hosts. It certainly looked like they were going to get that win too. They had racked up a solid score of 401 runs in the first innings, and gotten England all out for 174, forcing the home side to follow on. England needed 227 runs just to level the scores, with the Aussies still to have another go with the bat.

Towards the end of the first innings for the English batsmen, with them seemingly having no chance, the bookies must have thought it was all over and were offering massive odds of 500/1 for an England win.

Amazingly, it is believed that two of the Aussie players couldn’t resist that huge price and they actually bet on themselves to lose. Bowler Dennis Lillee and wicket keeper Rodney Marsh both placed a wager on England, against all odds to win the match, and in doing so netted themselves £7,500, a decent sum in those days.

Both players and the Aussie management denied the bets for a long time but over the years the truth has been made clear. Lillee had wanted to bet £50 of team money before being labelled mad but settled on a tenner of his own cash.

There has never been any suggestion that he or Marsh threw the game and it was simply the famous heroics of Ian Botham and the late Bob Willis that turned the game on its head. This truly was a crazy bet and sport, mad as we know it can be at times, duly obliged.

Ben Curtis Wins 2003 Open Championship at 300/1

Playing in his first major championship and ranked only 396th in the world rankings, Ben Curtis wasn’t even likely to make the cut for the Open Championship according to bookies. The American was essentially given no hope and having never played at a links course one could argue odds of 300/1 were rather skinny.

In the first two rounds he played nicely enough and was one over par for both. With conditions tough and scoring hard, this left him tied for third and only three shots behind. Curtis said that “Looking back, my whole goal there was just to have fun and play all four days” and so he really had nothing to lose going into the weekend.

Once again, in the third round he wasn’t pulling up any trees, but his play was steady enough and he did just enough to keep pace with the leaders, finishing only two shots behind Thomas Bjorn who was one under par.

Then in the final round Curtis really turned it on, with six birdies in the first 11 holes seeing him shoot up the leaderboard in style. He did stumble over the following six holes with four bogeys, but he went into the clubhouse with the lead.

Tiger Woods and Vijay Singh did try their best to reign him in but fell behind late on. It was Thomas Bjorn who gave Curtis the closest run and having a three stroke lead with four to play he looked a shoe in. Unfortunately for him two double bogeys in those holes cost him dearly, and Ben Curtis was able to lift the famous claret jug for the first and only time.
ESPN explained how remarkable this was, saying “it was surreal. Curtis began the final round two shots out of the lead and nobody was giving him a chance. Nobody — despite what they say today — knew who he was.” Nobody game him a chance and that makes this a truly crazy 300/1 long odds cracker!