The Biggest Upsets in Sports History
May 2, 2023

Sports betting is one of the most popular pastimes in the world, with millions of people placing wagers on their favorite teams and athletes every day. While most sports bettors are content to make small wagers and hope for modest returns, there are those who are always on the hunt for the next big upset.

Over the years, there have been many underdogs who have pulled off unlikely victories, shocking the sports world and winning big for those who placed bets on them. In this article, we will take a look at some of the biggest upsets in sports betting history, and explore what made these underdogs so successful.

One of the most famous upsets in sports history occurred in 1980, when the United States men’s hockey team defeated the heavily favored Soviet Union team in the Winter Olympics. The Soviet team had won the gold medal in the previous four Olympics and was widely considered to be the best hockey team in the world. But the American team, made up of amateur players, managed to pull off a stunning 4-3 victory, with goaltender Jim Craig making 36 saves.

The odds of the United States winning that game were as high as 1,000 to 1, meaning that anyone who had placed a bet on the underdog would have made a fortune. But what made this upset so remarkable was the fact that the Soviet team had dominated international hockey for years, and had beaten the United States 10-3 in a previous exhibition game just a few weeks earlier.

Another famous upset occurred in 2004, when the Boston Red Sox won the World Series, breaking an 86-year championship drought. The Red Sox were facing the New York Yankees in the American League Championship Series, and were down three games to none in the best-of-seven series. No team in baseball history had ever come back from such a deficit, but the Red Sox managed to win four straight games, including an epic Game 4 in which they overcame a 4-3 deficit in the bottom of the ninth inning.

The odds of the Red Sox winning the series after falling behind 3-0 were as high as 20 to 1, meaning that anyone who had placed a bet on them would have made a fortune. But what made this upset so memorable was the fact that the Red Sox had been plagued by bad luck and heartbreak for so many years, and that they had faced such a daunting task in trying to come back against the Yankees.

In the world of horse racing, there have been many upsets over the years, but perhaps none more surprising than the victory of 1913 Kentucky Derby winner Donerail. Donerail was a long shot, with odds of 91 to 1, but managed to win the race by a nose. This upset remains the biggest long shot to ever win the Kentucky Derby, and is still considered one of the greatest upsets in horse racing history.

The biggest upsets in each sport will inevitably be a matter of debate, but here are some of the most memorable upsets in various sports.

In soccer, the biggest upset was in 2016, when Leicester City, a team that had narrowly avoided relegation the previous season, shocked the football world by winning the English Premier League. The odds of Leicester City winning the league at the start of the season were as high as 5,000 to 1.

For football, in Super Bowl III in 1969, the New York Jets, led by quarterback Joe Namath, defeated the heavily favored Baltimore Colts, 16-7. The Jets were 18-point underdogs, and Namath famously guaranteed a victory before the game.

In the 2016 NBA Finals, the Cleveland Cavaliers, led by LeBron James, came back from a 3-1 deficit to defeat the Golden State Warriors, who had set a regular-season record for wins. The odds of the Cavaliers winning the series after falling behind 3-1 were as high as 10 to 1.

Meanwhile in baseball, you can look at the 1988 World Series, where the Los Angeles Dodgers, who had finished the regular season with a record of 94-67, defeated the heavily favored Oakland Athletics, who had won 104 games. The Dodgers were underdogs in every game of the series, and won in five games.

In the 2010 Winter Olympics, the Canadian men’s hockey team was heavily favored to win the gold medal, but were upset by the United States in the preliminary round. The Americans won 5-3, with Ryan Miller making 42 saves.

Most people remember or have heard about the biggest upset in boxing. In 1990, Buster Douglas shocked the boxing world by knocking out heavyweight champion Mike Tyson in the tenth round. Douglas was a 42-to-1 underdog, and had lost his previous two fights.

More recently in horse racing,  Mine That Bird, a long shot with odds of 50 to 1, won the 2009 Kentucky Derby by nearly seven lengths. The victory was one of the biggest upsets in the history of the Kentucky Derby.

In the 2004 Wimbledon final, Roger Federer, who had won the previous three Wimbledon titles, was upset by unseeded Croatian player Goran Ivanisevic. Ivanisevic, who had entered the tournament as a wild card, won in five sets.

In the 2003 Masters, Mike Weir became the first Canadian to win a major golf championship, and did so as a 40-to-1 underdog. Weir won in a playoff to win the green jacket.

Meanwhile in mixed martial arts, Anthony Ruiz Jr. defeated heavyweight champion Anthony Joshua in a stunning upset in 2019. Ruiz was a 25-to-1 underdog, but knocked Joshua down four times en route to a seventh-round TKO.

These are just a few examples of the many upsets that have occurred in various sports over the years. Regardless of the sport, upsets can be both thrilling and unpredictable, and are a testament to the unpredictable nature of athletic competition, and why even the biggest underdogs attract action where bettors are hoping for a huge payoff.

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