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The 20 Biggest Upsets in Sports History Ever Recorded

Betting 20 Biggest Upsets in Sports History
Nov 25, 2021 10:11Andrej Trajkovski

One of the reasons why people love sports is the element of surprise. Almost every match or sporting event has favorites and underdogs. Still, these predictions bookies make are based on stats, and it seems that these numbers sometimes mean nothing. In other words, you should expect the unexpected in many events.

Of course, some surprises are small, while others are almost incredible. The biggest upsets in sports history are written in the memory of true fans and sports commentators. To remind our readers of some of the biggest sporting upsets, we have created this detailed list. If you’re interested in the top 10 most heated sports rivalries, check it out here.

20. The Boston Red Sox win the 2004 World Series title

To be honest, this was not the first annual championship series of MLB won by the Boston Red Sox. This team has done this five times before, but Red Sox players held the trophy back in 1918 for the last time. So, it’s no surprise why this event is one of the biggest upsets in sports history.

Before reaching the finals, The Boston Red Sox entered the competition as the AL Wild Card. To get the trophy, they had to beat the New York Yankees, a team that was a big favorite. After all, they manage to beat Boston Red Sox in the first three games. Fans were preparing for another defeat in a row, but then things started changing. The initial 3-0 were turned into 4-3 in Boston Red Sox’s favor. This was a true baseball miracle.

19. The Amazin’ Mets – the New York Mets win the 1969 World Series

It looks like some of the biggest sporting upsets happened in the world of baseball. Back in 1969, the New York Mets were the underdogs in the finals against the Baltimore Orioles. One of the reasons for that was the Orioles’ powerful pitching rotations unmatched by any MLB team. It turned out that this wasn’t enough to stop the New York Mets.

This team won the series with a stunning score of 4 to 1. As a result, the team was nicknamed Amazin’ Mets or Miracle Mets.

18. Trevor Immelman Surprise Win at the 2008 Masters Tournament

Tiger Woods had his ups and downs, but 2008 was a good year for the world’s most famous golfer. At least that’s what everyone thought at the beginning of this year. He managed to win the US Open and won the PGA Championship the previous year.

All these results made fans think that he would win the Masters Tournament. The fact that the tournament was played in Augusta, Georgia, made it even easier to guess the winner. However, Trevor Immelman had other plans. The South African player ended up three strokes ahead of Tiger Woods and won his first major title.

17. Rulon Gardner wins his Olympic wrestling debut (2000)

Of course, every athlete must meet specific requirements to participate in the Olympics. Rulon Gardner from Wyoming, USA, was not an exception. Yet, he was an outsider and a relatively unknown name in the world of wrestling.

It was hard to imagine that this guy could defeat Alexander Karelin, a Russian wrestler. The latter already had three gold medals at the Olympics and numerous titles. However, that’s exactly what happened at the Sydney Olympics in 2000. This was one of the biggest upsets in sports history noticed by thousands of sports fans across the globe.

16. Leicester FC wins the 2016 Premier League title

Every new season in the Premier League brings exciting moments. After all, that’s why this is the most popular football/soccer league in the world. All the professional teams have exceptional football players. Still, truth be told, there are always a few teams that are ahead of everyone else. Typically, we are talking about the so-called Big Four or Big Five. The names of the teams that belong to this category are changing: Manchester United, Chelsea, Liverpool, Arsenal, Manchester City, etc.

One thing is for sure, Leicester FC was never part of this group of teams, and it definitely wasn’t there at the beginning of season 2015-16. To be more precise, the bookies predicted that the chances of winning the title for this team were 5000 to 1. With a dash of luck, the great chemistry in this team has helped them create one of the biggest upsets in sports history by getting their first Premier League title.

15. Greece becomes a European football/soccer champion (EURO 2004)

When the Greek national football team entered the Euro 2004 (European Football Championship), the nation had big hopes, but (almost) no one imagined that this team could actually win the competition. The first shock was in the opening match when they defeated the host Portugal (2-1). Yet they’ve lost Russia but still qualified in the next round.

In the finals, Greece met Portugal and defeated them again. This was an incredible journey for the Greek players, who were considered outsiders from the start since that was their second appearance in this competition. As a result, we had one of the biggest upsets in sports history, especially when it comes to football.

14. Coco Gauff beats Venus Williams (2019)

Sometimes you need to be a little bit cocky to become a winner. That’s the attitude of young Coco Gauff (15 years old at that time) when she appeared at the Wimbledon tennis match against Venus Williams. As we all know, Venus is one of the best tennis players of all time, but in 2019 she lost 2-0 to Gauff. Sadly, the young American tennis player didn’t win the tournament, but she had even better results after this match.

13. Golden State Warriors become NBA champions (1975)

Who says that basketball doesn’t contribute to the biggest sporting upsets? There are dozens of basketball matches, especially NBA matches, that can confirm this. The NBA finals in 1975 are an excellent example of that. The Washington Bullets (known as Washington Wizards today) were a huge favorite against the Warriors.

After the first three matches, the Warriors had a 3-0 lead. In the fourth match, the Bullets had a huge lead but managed to lose in the end. So, the Warriors became champions with a stunning 4-0 win.

12. The Chicago Blackhawks win the Stanley Cup (1938)

To be honest, this is not the latest, but it’s among the biggest upsets in sports history. Before reaching the playoffs, the Chicago Blackhawks have lost more matches than they have won. How is this possible? Well, only the team on the last position in its division didn’t make it to the playoffs back then.

Anyway, the Blackhawks somehow managed to get to the finals, and on top of that, they’ve defeated the Detroit Red Wings 3-1 (four matches).

11. Boris Becker wins Wimbledon (1985)

If you like tennis, then you’ve probably heard about Boris Becker. After all, this man has won six Grand slam titles, three of which at Wimbledon. So, what makes his win in Wimbledon in 1985 so unusual and incredible? In 1985, he was just 17 years old, and he managed to win the iconic tennis competition. Several well-established players, including John McEnroe, Jimmy Connors, and Ivan Lendl, were part of the tournament, but this didn’t stop Boris Becker from winning.

10. Belarus defeats Sweden at the 2002 Winter Olympics (Ice Hockey)

Ice hockey is a very dynamic sport, and that’s why it’s no surprise that some of the biggest sporting upsets are associated with this sport. Before the quarterfinals started, Sweden won three out of three matches while Belarus lost all three. Due to the specific rules, Belarus made progress to the quarterfinals.

Based on the results and the fact that just one player from the Belarussian ice hockey team was an NHL player while the Swedish team consisted of top-rated players, everyone thought that Sweden would be a clear winner. However. Belarus won 4-3 and eventually played for the bronze medal (they’ve lost 7-2 to Russia).

9. Naomi Osaka loss to Marketa Vondrousova at the 2020 Tokyo Olympics

It was not just the postponement of the 2020 Tokyo Olympics that made this tournament different than the others. A few surprises have made it more exciting. One of these examples involves Naomi Osaka, the famous Japanese tennis player. She opened the Olympics.

Naomi didn’t have problems in the first two rounds, but the (then) second-ranking player in the world faced Marketa Vondrousova (Czech Republic), the world’s 42nd best player at that moment. Marketa easily defeated Osaka and managed to get the silver medal.

8. James Hill defeats Ronnie O’Sullivan (2019)

If there’s one name that comes to our mind when someone mentions snooker, that must be Ronnie O’Sullivan. The eccentric player holds six Snooker World Championship titles. In 2019, he was focused on winning the seventh title, something that only Stephen Hendry has managed to do in the long history of snooker.

Unfortunately, O’Sullivan was defeated in the first round by James Cahill, an almost unknown name at the time. It was a match full of twists, but in the end, Cahill won 10-8.

7. New England Patriots win the 2002 NFL Super Bowl

Let’s be clear – the New England Patriots are not a bad team. On the contrary, they are always a tough opponent for the rest of the NFL teams. However, before 2002, they’ve won just one trophy (in 2001).

They were scheduled to meet the St. Louis Rams, a team with great results during that season. That’s why they were given a 14-point advantage in this match. However, the New England Patriots, led by Tom Brady, made one of the biggest upsets in sports history by defeating the Rams 20-17.

6. New York Giants win the 2007 NFL Super Bowl

We have another event from the NFL on this list and involves the New York Giants. In 2007, they entered the Super Bowl as outsiders against the New England Patriots, a team on fire during that season (they’ve won 16 out of 16 matches so far).

The match was tight, and there were many exciting moments, but the New York Giants won 17-14 in the end. This was their first title after 17 years.

5. The United States national soccer team defeats England at the 1950 FIFA World Cup

Even today the US national soccer team is not considered one of the best in the world. But, the situation was even worse in 1950 when the USA usually lost all their matches against European teams. This is the reason why people believed that England would win against the US in the early stage of the competition by (at least) three goals margin.

The completely opposite happens after 90 minutes. It was a 1-0 victory for the USA. The goal was scored by Gaetjens in the first half. So, there was a lot of time for the English team to bounce back, but they didn’t have the strength to do that.

4. The US national hockey team defeats the Soviet Union (1980)

You’ve probably heard about the Miracle on Ice, right? We must mention this event again when we are talking about the biggest upsets in sports history. The 1980 Winter Olympics took place in Lake Placid, US. It looks like the home ground was a massive advantage for the US national ice hockey team. Even though the Soviet Union was the favorite in the final match, the US won 4-3. The Soviet Union had a lead at one point, but that didn’t stop the bold US team from turning the match in its favor.

3. Mike Tyson loses to Buster Douglas (1990)

It’s always nice to see underdogs winning against established athletes. That makes sports more enjoyable. When Mike Tyson met Buster Douglas in 1990, he was not only the boxing heavyweight champion of the world, but he was also undefeated. According to many sources, Tyson decided to fight Douglas to stay in shape for the upcoming match against Holyfield. However, the comeback of one of the world’s greatest boxers was a failure because he lost the game. The only good thing was that he wasn’t knocked out. This fight is also one of the all-time top 10 boxing upsets in hustory.

2. Jack Fleck wins the 1955 US Open titles

The US Open has been one of the most prestigious golf competitions in the world for many decades. It’s good to know that the same goes for the tournament held in 1955. The crème de la crème of the golf scene was present at the 1955 US Open, but there were also a few anonymous players. One of them was Jack Fleck, a golfer. He had played this sport professionally for just six months before going to the tournament. That’s why it was a big surprise when he won the title in the end.

1. Japan defeats South Africa at the 2015 Rugby World Cup

Wait, Japan has a Rugby team? If you are not a big fan of rugby, you probably don’t know that Japan has a long history in this sport (since 1866). Truth be told, the national team didn’t have great success over the years. They were part of 9 World Cups and managed to reach the quarterfinals just once. However, every now and then, they defeat “strong” opponents. Their success against South Africa at the 2015 Rugby World Cup is one of the biggest sporting upsets that the rugby world has seen. They’ve won 34-32, although the odds on an outcome like this were 80/1.

You’re asking yourself what’s next after reading this top list? Well, we have a few more for you. You should check out our 100 most memorable super bowl commercials of all time!

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Andrej Trajkovski
Lady Liberty
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As a gambling editor, Andrej aims to provide readers with everything new from the world of gambling. Since he is our columnist, his topics are often a bit more extensive and fun. Whether it’s analysis on the reunification of Ireland, Spotify gambling playlists, or history posts, he gets the job done.
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