The 3 Biggest Sportsbook Upsets Of The 21st Century

More often than not, examining the odds for a sporting event will give you a strong indicator of how that eventuality will play out. Sometimes the sportsbooks and gambling companies can get it slightly wrong, especially in certain sports where there’s a substantial margin of error due to several variables to weigh up.  One of the best examples is horse racing, where you often get horses with odds of 5.00 or 10.00 winning races. In horse races like The Grand National, you sometimes see horses with decimal odds of 60.00 or 70.00 leading out in the front pack for large portions of the race; such is the unpredictability of this particular sporting event.

When you compare some of these upsets to odds you might see in traditional casino games, even table games like roulette, where you’ll get substantial decimal odds of 35.00 for an individual number, are far more likely to occur than some of the biggest upsets in The Grand National. However, the biggest sportsbook upsets of the last 23 years make these odds look like odds on favorites.

Biggest Sporting Upsets Of All Time

Although today’s focus is on the 21st Century upsets, some of the biggest upsets of all time include Mike Tyson vs. Buster Douglas in 1990 and the Australian Mark Edmonson, ranked outside the top 200 in the world at the time, who won the Australian Open in 1976. He is the lowest-ranked player ever to win a grand slam title and defeated fellow Aussie John Newcombe, who was defending his title after beating American tennis great Jimmy Connors in 1975.

Connors had a vested interest in casino gaming and invested many of his winnings into business ventures, such as owning two casinos in Missouri, so he knows all about gambling markets and sporting upsets.

However, the casino gaming landscape has changed since the 1970s. Aussies looking to gamble need to look no further to see the changes in the face of Ignition Casino Australia and its selection of table-based games. While land-based casinos still do well, digital casinos are ramping up their operations. Providing stiff competition with an excellent range of games and bonuses that you can take advantage of without having the inconvenience of having to travel to a physical location.

#3 – Boston Red Sox Win The 2004 World Series

For many baseball fans, the Red Sox World Series win in 2004 was the most significant moment in American baseball history, mainly due to the incredible odds they overcame to become the champions. With odds of 120.00 going into the game, meaning if you put $10 on them, you would have won $1,200, it was unimaginable for most experts and analysts to predict a Red Sox win, with everybody unanimously predicting a significant win for the St Louis Cardinals.

The game involved historical significance as the legendary “Curse Of The Bambino” was finally broken. Before Babe Ruth dominated baseball and became one of the most dominant and legendary figures in American sport, the Red Sox were a solid outfit, consistently challenging for the top trophies in baseball and winning multiple series. However, when they defied all odds and won the World Series in 2004, they ended a drought that had existed for nearly 90 years, making the remarkable upset much more special for Red Sox fans.

#2 – Cardinals Win The World Series – 2011

In another game that featured the Cardinals, they were a staggering 900.00 to win with some sportsbooks, and some even reportedly had markets for them at 999.00, meaning a $1 would have returned you $1,000. Not a bad return!

It seemed as though the Texas Rangers were destined to lift their first World Series, playing fantastic baseball throughout the season and consistently performing when it mattered, only to fall at the final hurdle. David Freese was the star performer as the Cardinals defied the odds and reversed the roles of the 2004 final when they lost despite having the backing of every analyst and expert in the game.

#1 – Leicester City Win English Premier League – 2016

The most significant statistical anomaly in 21st-century sport is when Leicester City won the English Premier League in the 2015/16 season. Just two years earlier, they were playing their football in the second tier of the English professional leagues, and following a 14th-place finish the year before, nobody even predicted they would finish in the top half in the 2015/16 campaign.

However, inspired performances from world-class players such as Jamie Vardy and Riyad Mahrez, Leicester City, at odds of 5000.00, managed to comfortably win the league, beating the likes of Chelsea, Manchester City, and Manchester United. If you’d put $10 on Leicester City to win the Premier League, you’d have won $50,000!

It’s unlikely we will ever see anything like this again, especially during a 38-game league campaign. Once in a generation, you might have a team that manages to win a knockout tournament or a cup, despite tremendous odds saying otherwise. However, consistently performing for nine months with a team many believed wasn’t even in the top 10 is genuinely astonishing. Even top sportsbooks tipsters had no idea Leicester City had it in them to go on such a remarkable run and easily beat the cream of English football to lift the domestic title.

English sports won’t see anything like this again for a long time, that’s for sure, and it could be decades before we witness anything like this in any sport. It is difficult to comprehend these odds, and they will never be forgotten by people who watched them unfold in real-time.

Leave a comment

Free Betting Tips, Direct to Your Inbox

Sign Up Today to Join Betting Gods for FREE and Receive Betting Tips Direct to Your Inbox Every Morning

Not Sure Who to Join?

These are the Top Performing Tipsters in April

In Form

Punter's Profit Pro

194 Winners Since May 2023
Total Profit:£4,985.20


Per Month


Win Rate




This Month

In Form

Racing Rundown

333 Winners Since August 2022
Total Profit:£7,982.00


Per Month


Win Rate




This Month


Just Winners

81 Winners Since October 2023
Total Profit:£4,090.25


Per Month


Win Rate




This Month