The 11 Biggest Long Shots in Sports That Paid Off Big

The old saying goes that there’s no reward without risk. That’s the nature of sports gambling. You risk money, and if you guess correctly, you’re rewarded.

The reward is based on how much of a risk you take. This is a combination of the money you wager and the odds that are given on the event.

As a general rule, most people will make reasonable bets that pay off a modest amount in return.

A bet that a champion boxer will retain their title is an example of a reasonable bet. A bet that a team leading their division will win a game is another example of a reasonable bet.

But what happens when you make an unreasonable bet — a bet that’s a long shot to win?

In the majority of these cases, you’ve just kissed your money goodbye.

But that’s not always the case.

Much like life itself, strange things can happen. For instance, Major League Baseball’s Boston Red Sox were perennial losers when it came to the World Series for 86 years. They finally broke “the curse of the Bambino” in 2004. Since then, they’ve become a powerhouse in the MLB, winning three more World Series since 2004.

When they won in 2004, they hadn’t even won an American League Championship in 18 years, and the way they lost the World Series to the Mets in 1986 was truly indicative of a team that was cursed.

While the Red Sox were expected to lose the 2004 World Series simply because history seemed to dictate it, they weren’t long shots.

In the modern history of sports, there have been many individuals and teams that were in much less of a position to win a game, a match, or an event. Yet, defying the oddsmakers, they succeeded and left the critics and oddsmakers with their jaws dropped wide open in astonishment. And for those who decided to take the risk, it made them very wealthy.

While the list I compiled isn’t comprehensive by any means, they represent some of the biggest long shots in history.

So let’s count down some of the biggest long shots in sports.

11 – Buster Douglas KOs Mike Tyson (42 to 1)

In the late 1980s, Mike Tyson seemed unstoppable. He was undefeated. His matches rarely went past three rounds, and in less than ten months in 1986-1987, he became the first man ever to unify the three major heavyweight boxing championships at the time: the World Boxing Council, the World Boxing Association, and the International Boxing Federation World Heavyweight Boxing Championships.

In 1988, The Ring magazine also named him the Ring and recognized him as the lineal World Heavyweight Boxing Champion after beating Michael Spinks in the first round of their fight.

Over the next two years, Tyson would build up his record to 37 wins, 0 losses.

On February 11, 1990, a relatively unknown fighter would face Tyson for the undisputed championship. His name was Buster Douglas.

Most people dismissed Douglas’ chances of winning. After all, Tyson’s previous five fights (all scheduled for 12 rounds) totaled only 13 rounds, each ending with decisive victories.

Las Vegas oddsmakers had set Douglas’ odds of winning the belts at 42 to 1. But despite the opinion of, in essence, the world, Douglas shocked everyone to knock out Tyson in 1:22 in the tenth round to win the five championships.

Obviously, there was controversy. Some questioned the cadence of the referee’s count. Some blamed the fact that it was Tyson’s first fight outside of the United States.

Some even thought that Tyson intentionally dropped the belts because of dwindling pay-per-view buys on his matches due to the extreme number of first- and second-round victories. The idea was that he lost on purpose to generate interest in a rematch that would stimulate record pay-per-view purchases of the rematch.

Tyson’s promoter Don King protested the title changes with the sanctioning bodies. After four days of protests, Tyson’s camp dropped the challenges to the decision, and Douglas was the true champion.

Someone that bet $1,000 on Douglas to win the fight would have pocketed $42,000.

Douglas’ title reign was cut short as he lost the championships on his first title defense to Evander Holyfield.

10 – 2009 Kentucky Derby Winner Mine That Bird (50 to 1)

It is known as the most exciting two minutes in sports. The Kentucky Derby , with all its pageantry and tradition, is the most well-known horse race in the United States, if not the world.

On the night of May 1 and the early morning of May 2, 2009, the city of Louisville experienced heavy downpour.

This made less than ideal conditions for the Kentucky Derby as the Churchill Downs dirt track was rated “sloppy” for the race.

The 19-horse field listed odds for Mine That Bird as third from the bottom, with a 50-1 payoff.

Bird had trouble coming out of the gate and was soon several lengths behind all the other horses. He was so far back that television commentators couldn’t see him on the screen.

When heading into the backstretch, the jockey turned up the heat, and Bird caught up and started passing other horses.

He was so fast that neither the TV commentators nor the racers saw him coming until he was already leading by three lengths.

Mine That Bird wound up winning by six and three-quarter lengths, the largest margin in over 60 years.

It was the second-biggest upset in Kentucky Derby history.

9 – 1913 Kentucky Derby Winner Donerail (91-to-1)

Since I mentioned the second-greatest upset in Kentucky Derby history, it’s only fitting that I talk about the biggest upset in the history of the Derby.

During the race, the lead horse kept changing.

The biggest obstacle was a horse named Ten Point.

Donerail was having trouble breaking into the top three due to a horse named Roscoe Goose blocking his way.

As they headed into the stretch, Donerail was able to pass the other horses to challenge Ten Point.

As the race finished, Donerail took the lead and finished a half-length in front of Ten Point, setting a track record (at the time) of 2:04.80.

Donerail finished out his life as a sire for the horses of the US Cavalry.

A $2 bet for Donerail in that race yielded a $184.90 payout. That would be almost $5,000 in today’s money.

8 – Tampa Bay Rays 2008 American League Champs (125-to-1)

The Tampa Bay Rays looked like they were going to win the American League Championships after game four of the series.

But after game five, opinions started to change.

The series started off with the Boston Red Sox winning the first game. This loss fueled the Rays to win the next three games in a row. All they needed to do was win game five to go to the World Series.

Unfortunately, the Red Sox had other plans and handed Tampa Bay a painful 8-to-7 loss in game five.

Things didn’t get better for game six. The Red Sox won the game 4 to 2, bringing the series to three wins for Tampa Bay and three wins for Boston.

At this point, oddsmakers saw the momentum with the Red Sox. After all, they were the defending world champions and were on a roll with two consecutive wins.

By the time the game started, Tampa Bay had 125 to 1 odds of winning.

Boston took the early lead in game seven with a run in the first inning. Tampa Bay tied it up in the fourth. The next inning, they took the lead and never looked back. Tampa Bay won the game 3 to 1 and went on to face, and ultimately lose to, the Philadelphia Phillies in the World Series.

7 – Greece 2004 UEFA Euro (150-to-1)

Every four years, the Union of European Football Associations has the European Championships.

Greece isn’t necessarily considered a contender in these tournaments as they generally failed to qualify in previous years.

Oddsmakers listed them at the bottom of the barrel to win with 150 to 1 odds.

But it was different in 2004. Greece dominated the tournament, beating Portugal in the opening match, then knocking out England and the Netherlands.

In the final matchup, they faced the team they defeated first in the tournament, Portugal.

It was the first time in a major soccer tournament that the opening match and the ending match were the same.

Greece would make all detractors eat crow that year as they dominated Portugal again to take the Euro Championship.

6 – St. Louis Rams to Win Super Bowl XXXIV (300 to 1)

The Rams suffered lots of bad luck in the 1990s. They were actually among the worst teams in the league in that decade.

This is why when the season started in 1999, the futures bets on the Rams to win the Super Bowl was 300 to 1.

But the Rams silenced all of their detractors as the season went on. They finished the 16-game season with a record of 13 wins and 3 losses.

They would then defeat the Minnesota Vikings in the division playoffs and the Tampa Bay Buccaneers in the NFC Championship game to make it to the Super Bowl.

At Super Bowl XXXIV, the Rams faced the Tennessee Titans, who also finished the season with 13 wins and 3 losses.

Despite a second-half rally by the Titans, the Rams held the lead the entire game, winning the Championship 23 to 16.

Anyone who bet $100 on the Rams as the season started would have won $30,000.

5 – 2003 Ben Curtis Wins the British Open (300 to 1)

Sometimes, skill and determination win championships. Sometimes, it’s sheer luck. Sometimes, it’s a combination of both.

In the case of Ben Curtis, it would appear to be sheer luck.

Curtis was a fine journeyman golfer, and he made the cuts on several tournaments. But in 2003, going into the British Open, Curtis was not even considered a contender.

After all, he was ranked 396th in the world and was playing against the likes of Tiger Woods, Davis Love III, Greg Norman, and Nick Faldo.

For those not familiar with the British Open, or any tournament on the PGA circuit, the tournament consists of four days of 18-hole golf.

The scores for each day are added up, and the lowest score wins the tournament.

After day one, Hennie Otto, Davis Love III, and Greg Norman finished in the top three.

When day two was completed, Davis Love III, Thomas Bjørn, and S.K. Ho had taken the top three spots.

The third day saw Thomas Bjørn, Davis Love III, and Ben Curtis finish in the top three.

The final round was the shocker as Ben Curtis shot a 69 on the course to beat out Thomas Bjørn and Vijay Singh by one stroke to win his first major tournament.

I mentioned that it was more luck than anything. And I believe that to be true because that was the only major tournament that Curtis would ever win.

4 – 1987 Minnesota Twins (500 to 1)

In 1987, the Minnesota Twins hadn’t won a World Series since they were known as the Washington Senators in 1924.

When the season started, oddsmakers believed that the 63-year dry spell would continue. Especially since they hadn’t won a division since 1970 or the league championships since 1965.

But Minnesota made changes prior to the 1987 season.

One of the first moves management made was the hiring of Tom Kelly as the new manager during the 1986 season. He started to rebuild the team from scratch.

A series of trades in the off-season were made, and a few new free agents were signed.

At the beginning of the season, oddsmakers took into account the historical record of the Twins as well as the belief that they were in a weak league to determine the 500 to 1 odds of them winning the World Series.

And to be honest, the team did okay, but they were far from stellar. They finished the season with 85 wins and 77 losses. This was a winning percentage of .525.

But despite this, they went on to defeat the Kansas City Royals and the team with the best record in baseball that year, the Detroit Tigers.

They would go on to defeat the St. Louis Cardinals four games to three in the World Series.

The Twins had the worst record of any team to win the World Series up until that time.

For anyone who bet $100 at the beginning of the season on the Twins to take it all, they would have won $50,000.

3 – 2011 St. Louis Cardinals (999 to 1)

At the beginning of the season, the Cardinals were seen as a viable team to win the World Series. They had won the Series in 2006 and had respectable showings in years prior.

But as the season went on, prospects grew bleaker as to their chances of even getting into the division championships as with 15 games left in the season, they were four and a half games behind the leader.

Oddsmakers had set the odds of them winning the World Series at 999 to 1.

What happened in the last 15 games was nothing short of miraculous.

The Cards would go on a rally that saw them win 11 of their last 15 games. This would clinch them a wild card spot and a chance at the National League Division Series.

The Cardinals faced the Philadelphia Phillies in the NLDS. They beat them three games to two.

Next, the Cardinals faced the Milwaukee Brewers in the National League Championships. They beat them four games to two. This sent them to the World Series.

The Cardinals faced the Texas Rangers in the World Series. In a back and forth series, St. Louis defeated the Rangers four games to three to capture the championship.

If any person had the foresight to bet on the Cardinals to win the World Series with 15 games left in the season, a $100 bet would have won $99,900.

2 – 1980 Miracle on Ice (1000 to 1)

The 1980 United States Olympic Hockey Team was the ultimate underdog story.

The team wasn’t expected to go far. The USSR Hockey team had won the last five Olympics and was expected to win in 1980.

But the USA team had different ideas.

The journey started with a last-minute goal in a game with Sweden, who was heavily favored to be in the medal round. The goal would tie the game and keep the USA team’s hopes alive.

The next four games showed that the US was there to play as they scored the following victories:

  • Czechoslovakia 7-3
  • Norway 5-1
  • Romania 7-2
  • West Germany 4-2

These victories led to the inevitable matchup against the USSR team. In the third period, the US team would tie up the score to 3 to 3. And with ten minutes left in the period, the US would score the lead goal. The US would hold off the Soviets for the remainder of the game, winning the game and clinching the gold medal.

A bet of $1,000 on the US team to win the gold would have had a $100,000 payoff.

1 – Vegas Golden Knights (500 to 1)

So, I’ll start this by saying that the Golden Knights didn’t win the Stanley Cup. But I’ve included them because they were given no chance to even make it to the Stanley Cup.

It was their first year in existence after all.

The Golden Knights defied all odds, and, as some sports betting analysts have said, changed the way oddsmakers look at futures betting.

At the beginning of the season, the Golden Knights were given the worst odds in the league to win the Cup at 500 to 1.

By the time that the Stanley Cup rolled around, sportsbooks were shaking in their shoes at the possibility of payoffs in the tens of millions of dollars.

After game one of the series, oddsmakers were even more nervous as they beat the Washington Capitals 6 to 4.

That would be the end of their fears, though, as the Capitals won the next four games to win the Stanley Cup.

But an important lesson was learned by oddsmakers — never underestimate unknown quantities.

Honorable Mention

In addition to the list I’ve brought you, I have a few more that deserve a quick mention.

2015 Premier League – Leicester City (5,000 to 1) – The English soccer league team rarely finished in the top five, but 2015 was a weird year for the Premier League, and the team that had odds every year varying from 2,000 to 1 to 5,000 to 1 actually won the league title.

Greco-Roman Wrestler Rulon Gardner – 2000 Summer Olympics (2,000 to 1) – Gardner was not even viewed as someone who would win a medal at the games. It was expected that Russian Alexander Karelin would win the medal. Karelin was undefeated for 12 years, and Gardner never finished higher than fifth in competition. Gardner would shock the world by pinning Karelin and winning the gold.


If you look at a sportsbook, you’ll see that there are always long shots listed somewhere on their site.

These bets are tempting because of the high payouts. But the reason they have crazy odds is that in all likelihood, they aren’t going to have to pay off.

The examples listed here are exceptions to the rule and not the rule itself.

Long shots are extremely risky.

Do I bet on long shots? Yes, I do. Do I bet a lot of money on long shots? No, I don’t. I’ll throw $5 here and there, but I won’t bet hundreds or thousands on these matchups.

But the stories are great. And having the foresight to bet on them is even better. It’s the American dream.

Michael Stevens

Michael Stevens has been researching and writing topics involving the gambling industry for well over a decade now and is considered an expert on all things casino and sports betting. Michael has been writing for since early 2016.

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