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7 Longshot Wins in the History of Sports Betting

| November 26, 2021 6:25 am PDT

Is there a better feeling for a sports bettor than hitting a big long shot? You get the money and maybe more importantly, the bragging right to everyone who doubted you. Okay, maybe the money is better.

Although, it goes beyond just the bettor. These individuals and teams overcame the odds and did what nearly no one thought was possible. In simpler terms, they defied the odds.

So, let’s look at the biggest longshots in sports history.

7. 1990 Buster Douglas Over Mike Tyson (42-1)

When it comes to the best boxers of all time, Mike Tyson is at the top of a lot of lists. Iron Mike was basically unstoppable in his heyday.

On February 11, 1990, Tyson traveled to Japan to fight James “Buster” Douglas. Douglas wasn’t a bad fighter by any means. He came into the match with a 29-4-1 record with 19 knockouts. That only paled in comparison to Tyson’s 37-0 record with 33 knockouts.

It wasn’t a matter of who would win. It was a matter of how long would it take Tyson to knock Douglas out?

I can’t imagine anyone could’ve predicted what happened next.

Douglas came out swinging, controlling the early rounds.

Midway through the fight, Tyson’s eye began to swell up. It severely diminished his vision and he had a hard time seeing Douglas’ punches.

At the end of the eighth round, Tyson finally landed a punch that knocked Douglas to the floor. Douglas barely beat the 10-second count to keep the fight going.

The ninth round was all Douglas, as Tyson’s eye was completely shut at this point. That set the stage for a historic 10th round.

Douglas had a vicious uppercut that sent Tyson stumbling. Douglas continued with a few hooks that dropped Tyson for the first time in his career. Tyson tried to get up but he couldn’t beat the count.

At that point in the fight, the official scorecards had Douglas earning the win. The knockout was just the icing on the cake.

This fight remains the biggest upset in boxing history. No one was on Tyson’s level. Rarely did they ever go all 12 rounds. This time, it was Tyson that couldn’t make it to the end.

To this day, everyone remembers the name James “Buster” Douglas.

6. 1987 Minnesota Twins (500-1)

In 1986, only three teams finished with a worse record than the Minnesota Twins. That prompted some wholesale changes for 1987.

Minnesota hired Tom Kelly as their manager and brought in a few new faces. The moves didn’t impress the sportsbooks, as the Twins opened the season with 500-1 odds to win the World Series.

While the Twins looked much better this season, they weren’t a great team. In July and August, they had a combined 26-29 record.

The biggest thing going for the Twins was they played in a terrible division. They managed to win the division with an 85-77 record. For comparison, four teams in the AL East finished with at least 89 wins.

Minnesota can thank their home record for the postseason berth.

Check out their record at home compared to on the road.

  • Home: 56-25
  • Road: 29-52

In the ALCS, Minnesota faced off with a Detroit Tigers team that finished with an MLB best 98 wins.

Behind a powerful offense, Minnesota defeated Detroit in five games. The Twins scored at least five runs in all five games.

The World Series pitted the Twins against the St. Louis Cardinals. With Minnesota’s home and away splits, it only makes sense that they failed to win a single road game in the series. However, they did have home-field advantage thanks to the AL winning the all-star game.

After falling behind 3-2, Minnesota won the final two games to capture the World Series.

Minnesota defied the odds all season. No one gave them a chance at the beginning of the season and they were the underdog when they entered the playoffs.

We know the Twins never lost hope and knew they could win it all. As a 500-1 longshot, that’s exactly what they did.

5. 2003 Open Championship Ben Curtis (300-1)

Ben Curtis was a relatively unknown player going into the 2003 Open Championship. He was ranked 396th in the world and had never played in a major. That all contributed to him opening with 300-1 odds.

Curtis had two birdies and three bogeys in a six-hole span on the front nine. He finished the first round four shots behind leader Hennie Otto.

His second round was the same story. Two birdies and three bogeys led to his second straight 72. With the leaders dropping back, Curtin sat just three back going into the third round.

In the third round, Curtis had three bogeys and one birdie on the front nine. Just when it looked like his hopes were slipping away. He went -3 on the back nine to end the day +1 for the tournament. He sat two shots behind Thomas Bjorn.

Despite being within striking range, Curtis went into the final round with 40-1 odds. All I have to say is, I hope bettors took advantage.

Curtis came flying out the gates. He birdied his first hole en route to a -4 front nine. Birdies on 10 and 11 moved him to -5 for the tournament. Bjorn was the only one within striking distance at -3.

From there, Curtis learned how hard it is to close out a major.

Check out his score on the ensuing four holes.

  • 12: Bogey
  • 13: Par
  • 14: Bogey
  • 15: Bogey

Following a bogey on 17, Curtis sat three shots behind Bjorn, who had just birdied the 14th hole.

Bjorn shot +4 on his next three holes to fall one behind Curtis. A par on the last gave Curtis a one-shot lead.

Did he get a little lucky with Bjorn’s collapse? Absolutely, but it takes a little luck to win majors.

Curtis showed off his talent to win the 2003 Open Championship.

4. 1999 St. Louis Rams (300-1)

The St. Louis Rams were consistently one of the worst teams in the league in the 1990s. From 1990-1998, their best mark was 7-9 in 1995.

Before the season even started, the Rams faced adversity. After signing Trent Green, they traded starting quarterback Tony Banks. In the preseason, Green went down with a season-ending knee injury. That opened the door for unknown commodity Kurt Warner.

With Warner at the helm, the Rams engineered “The Greatest Show on Turf.”

St. Louis opened the season with six straight wins. Their high-flying offense scored at least 27 points in every game.

Following back-to-back losses. St. Louis went on a seven-game win streak. They rested their starters in Week 17, falling to the Philadelphia Eagles.

Warner went on to win MVP with these numbers.

  • 65.1 completion percentage
  • 4,353 yards
  • 41 touchdowns
  • 13 interceptions

Marshall Faulk also had a fantastic season with 1,381 rushing yards and 1,048 receiving yards.

The Rams offense was on full display in their 49-37 victory in the divisional round. Warner passed for 391 yards and five touchdowns.

In a defensive battle, the Rams knocked off the Tampa Bay Buccaneers 11-6 to advance to the Super Bowl. Warner threw the only touchdown of the game with just under five minutes remaining.

For the second straight game, the Rams were in a defensive battle. They led 16-0 before the Tennessee Titans tied the game with just over two minutes remaining.

On the first play of the ensuing drive, Warner threw a 73-yard touchdown pass to Isaac Bruce.

Tennessee worked their way down the field and found themselves on the 10-yard line with six seconds remaining.

Kevin Dyson caught the ball but was tackled one-yard short, giving the Rams a 23-16 victory.

A thrilling finish capped off one of the biggest longshots in NFL history.

3. 2011 St. Louis Cardinals (999-1)

St. Louis makes the list again but this time, it’s on the diamond.

Unlike most longshots we see, this one didn’t come at the beginning of the season. The St. Louis Cardinals had 999-1 odds to win the World Series in September.

Following a loss to the Pittsburgh Pirates, the Cardinals were 79-68. They sat four and a half games behind the Atlanta Braves for the wild-card spot. With 15 games left in the season, no one gave them a chance.

That’s when the Cardinals turned it on and the Braves collapsed.

St. Louis closed the season 11-4, while the Braves went 5-9. The Cardinals claimed the wild card by one game.

From there, they were on a mission to prove the doubters wrong.

The Cardinals trailed 2-1 in the NLDS before winning the final two games over the 102-win Philadelphia Phillies. The victory set up an NLCS matchup with the Milwaukee Brewers.

It was a 2-2 series before St. Louis won games five and six to advance to the World Series.

Just like the NLCS, the teams split the first four games. Only this time, the Cardinals were on the brink of elimination following a Game 5 loss. That set the stage for one of the greatest games in World Series history.

Down to their final strike, David Freese hit a two-run triple to tie the game. In the bottom of the 10th, the Cardinals were down to their final strike again. This time, Lance Berkman tied the game with an RBI single.

In the 11th inning, David Freese hit a walk-off home run to send it to Game 7. The Cardinals 6-2 win in Game 7 capped off the biggest World Series comeback in MLB history.

So many times, it looked like the Cardinals would fall short. They just kept fighting back and pulled it off as a long shot.

2. 2015-16 Leicester City (5,000-1)

For years, Leicester City was one of those teams that was either at the bottom of the Premier League, or relegated to a lower league.

In 2014-15, Leicester City needed a late-season surge to avoid relegation. That kept them alive for another season in the Premier League.

No one expected much from Leicester City in 2015-16. After all, they finished 14th out of 20 teams the season before. They weren’t going to let the low expectations stop them.

They had three wins and three draws in their first six games. A 5-2 loss to Arsenal dropped them to sixth in the league. That turned out to be their lowest ranking of the season.

Following the loss, they went unbeaten for 10 straight games. That stretch included wins over Chelsea and Everton. They also had a 1-1 draw against Manchester United.

A 1-0 loss to Liverpool briefly dropped them to second, but they moved back into first three matches later.

From there, they continued their winning ways. They only lost once in their final 20 games.

Leicester City officially clinched the Premier League title with two matches remaining.

Here are their final numbers from the season.

  • 23 wins
  • 12 draws
  • 3 losses
  • 68 goals scored
  • 32 goals allowed

Jamie Vardy and Riyad Mahrez did most of the goal-scoring, as they combined for 41.

With most sports, you have a cycle where almost every team has at least one great year. Before 2015-16, that never happened to Leicester City.

In the time they were in the Premier League, they never finished better than eighth. It makes their accomplishment that much more historic.

I bet soccer fans loved seeing a new team rise to the top. I know people who took a chance on them were ecstatic.

1. 1980 Team USA Hockey (1,000-1)

Doesn’t it seem like every big upset or longshot gets compared to the 1980 Team USA hockey team?

Team USA fielded a roster that mostly consisted of college players. That had nothing on the Soviet Union. Their roster consisted of professional players with a ton of experience. They had won the Gold Medal in five of the last six Olympics.

A late goal earned Team USA a draw in their opening match against Sweden. Team USA won the remainder of their games in the group stage in dominant fashion.

  • USA vs. Czechoslovakia: 7-3
  • USA vs. Norway: 5-1
  • USA vs. Romania: 7-2
  • West Germany vs. USA: 2-4

The success allowed Team USA to advance to the medal round. Their first matchup came against the Soviet Union. A few months before the Olympics, the Soviet Union put a beatdown on Team USA with a 10-3 victory.

This time, things were a little different.

Team USA was facing a 2-1 deficit when they scored in the final seconds of the first period.

The Soviet Union outshot Team USA 12-2 in the second period. They scored the go-ahead goal to give them a 3-2 lead going into the third.

In a two-minute span, Team USA scored a pair of goals to take a 4-3 lead. The Soviet Union had 10 minutes left to tie the game.

Over the final 10 minutes, the Soviet Union couldn’t find the back of the net. The final second prompted this call from Al Michaels.

“11 seconds, you’ve got 10 seconds, the countdown going on right now! Morrow, up to Silk. Five seconds left in the game. Do you believe in miracles? Yes!”

Team USA went on to defeat Finland in the Gold Medal game.

Sports fan or not, everyone knows the “Miracle on Ice.” The iconic moment was one of the biggest upsets in Olympic history.

Other Big Sports Longshots

  • 2000 Olympics Rulon Gardner (1,000-1)
  • 1913 Kentucky Derby Donerali (91-1)

Coming into the 2000 Olympics, Aleksandr Karelin had a 13-year undefeated streak in international wrestling. Karelin was looking for his fourth straight Gold Medal when Rulon Gardner upset him in the Gold Medal match.

In the 1913 Kentucky Derby, Donerali entered as a 91-1 longshot. Ten Point was the favorite and led into the stretch. That’s when Donerali ran him down, pulling off the biggest longshot victory in Kentucky Derby history.

Can you imagine hitting one of these bets? The first step towards doing so is checking out the top sports betting sites.

Nicholas Sterling

Nicholas has been a Sports Writer with GamblingSites.com since May 2021. He has a rich sports background, writing about NASCAR, NFL, NBA, MLB, NHL, Golf, etc. Nick is always ready for a new challenge.

He enjoys rooting on D.C. sports teams, including the Commanders, Wizards, and Capitals.

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