Five of the Biggest Betting Upsets in Sports History

Five of the Biggest Betting Upsets in Sports History
Image © Jeremy Brevard-USA TODAY Sports
✍️ Written by
Frank Weber
🗓 Updated
May 19th 2023

Every sports fan on the face of the Earth loves a good Cinderella story. In fact, some of the most memorable sports moments throughout history happened as a result of big underdogs putting together upset performances.

Moments like that are why we watch sports in the first place, no? If the favorite were to win everytime, what would be the point? It’s important to praise and remember the underdogs throughout history, because they are what makes sports so great.

The beautiful thing about an underdog story is that you can find it anywhere: The NFL, the NBA, the MLB–even horseracing and UFC have Cinderella stories of their own. If you are interested in trying to find the foot that fits your glass slipper, click HERE to find the best sportsbooks in your area.

And now, without further ado, here are some of the biggest betting upsets in sports history.

1. Leicester City to Win the Premier League in 2016 (5,000-1)

It’s times like this where we all wish we had Doc Brown’s Delorean and Marty McFly’s sports almanac. Even a $10 bet on Leicester City to win the Premier League in 2016 would get you enough money to buy a handful of Deloreans of your own. But unfortunately, hindsight is 20-20, so all you can do is admire the single biggest upset in sports history.

Yes, sports history. The entire thing.

To put this in perspective for American fans, the Baltimore Orioles currently stand at +50,000 odds on BetMGM to win the 2022 World Series, which are the worst odds in the league. Multiply that over a few times and then maybe you will reach what Leicester City accomplished in 2016.

To this day Leicester City remains in the Premier League but has yet to find the same success they found in that 2015-16 season. Some may be inclined to call this a fluke, but remember: fluke are some of the most common fish in the ocean, so if you go fishing for a fluke, chances are you’ll find one.

2. Rulon Gardner defeats Aleksander Karelin for Gold (2,000-1)

At the 2000 Olympic Games in Sydney, the world bore witness to one of the greatest upsets in sports history. The gold medal 130kg Greco-Roman match was all set as American Rulon Gardner stood opposite of Russian legend Aleksandr Karelin. Karelin came into the match on a 13-year undefeated streak, which included winning world-level titles every year from 1988 to 1999, and winning the 130kg gold medal in the last three Olympic Games.

The consensus was that Rulon Gardner would just be a small pebble in the road for Karelin as he went for his fourth gold medal, and that was reflected greatly in the event’s odds; Gardner came in as a 2,000-1 underdog.

However, on the worlds biggest stage, Gardner was able to deliver and secure a 1-0 victory over the previously unbeaten Karelin. The American became an overnight sensation, and will forever be remembered as the biggest betting upset in Olympic history…

…Well, I’m sure our next entry will have something to say about that.

3. Miracle on Ice: USA Defeats the USSR (1,000-1)

Often considered the biggest and most important upset in US history, the US Men’s Ice Hockey win over the Soviet Union in the 1980 Winter Olympics is one of the most iconic Hockey games of all time. The Soviets were heavy favorites coming in the game, as they were a team full of experience and skill. The Americans, on the other hand, were a ragtag group made up of mostly college-level nobodies (sorry).

After being down 3-2 coming into the start of the final period, team USA was able to grab two third period goals to secure the win and a spot in the gold medal game. The game will forever be cemented in history as “The Miracle on Ice,” thanks to ABC commentator Al Michaels’ waxing poetic call: “Do you believe in miracles? YES!”

4. St. Louis Cardinals win the 2011 World Series (999-1)

With less than three weeks left in the season, the St. Louis Cardinals were 4 ½ games behind the Atlanta Braves for the NL Wild Card Spot. Vegas sportsbooks had them dead in the water, with some listing odds as high as 999-1. But, thanks to a late-season collapse by the Braves and a stretch of wins by the Cardinals, St. Louis was able to sneak their way into the postseason, which would’ve been a success in and of itself.

But it doesn’t stop there.

The Cardinals went on to beat the Rangers in game 7 of the 2011 World Series, cementing their spot as one of (if not the) biggest World Series upsets in MLB history.

5. St Louis Rams win the 1999/2000 Superbowl (300-1)

There’s something about St. Louis and upsets, and I’m not quite sure what it is.

The Rams in the late ’90s were horrible–they had nine consecutive losing seasons coming into that 1999 season, and their star free-agent QB signing (Trent Green) got hurt before the season even began. So, out came Kurt Warner–who kickstarted a Hall of Fame career with one of the best season to date. Warner threw for over 4300 yards with 41 touchdowns, and led the Rams to an 11-5 regular-season record.

What ensued next was a postseason filled with close games and drama, but the Rams eventually succeeded and hoisted the Lombardi Trophy.

Honorable Mentions:

Red Sox win the 2004 World Series (120-1)

Buster Douglas defeats Mike Tyson (42-1)

#16 UMBC defeats #1 Virginia in the First Round of 2018 March Madness(20-1)

Holly Holm defeats Ronda Rousey (9-1)

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About the author
Frank Weber
Frank Weber
Sports Journalist & Betting Analyst

Frank Weber is a sports & gaming writer with a Bachelor's Degree in Journalism and years of experience in the gambling world. He loves baseball, football, basketball, soccer, and the UFC - he even collects sports cards and memorabilia! In his free time, you could find Frank either out at a concert with friends, or at home sweating out all his (soon to be won) bets!

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