The Biggest Underdog Pay-outs in Sports History

How many times have we seen a favourite be toppled by an underdog? Sport is so unpredictable that it does happen on a fairly regular basis – even at the biggest sport betting events.

But how about absolute giant-killings? Where a so-called “nailed on” favorite is bested by a minnow, a nobody or a complete unknown. This kind of occurrence is rarer but, when it does happen, it can cause shockwaves throughout the world of sport.

A good old-fashioned underdog story can also be a goldmine for anyone who had the foresight (or pure luck) to think about having a flutter on the unlikely outcome.

This article highlights exactly that as we run through the 9 most shocking and biggest underdog pay-outs in sports history.

Donerail in the 1913 Kentucky Derby at 91.45-1

According to the experts of online-gambling.com, who provide lots of information about online gambling NZ & US, Kentucky was just one of 2 states where horse racing was legal at this time.

In the 1913 Kentucky derby, most people could only envision one outcome: victory for 1.2-1 favorite: Ten Point. In the unlikely event that Ten Point didn’t get the win, there would not have been many people who were pinning their hopes on Donerail at over 91-1.

Once the race did get going, Donerail looked a different horse from the one who had claimed just 5^th a few days earlier in Lexington. In fact, he absolutely flew and won the race with a new Derby record time of 2.08.80.

Ten Point, the pre-race favorite, managed to come in at 2^nd.

This most unlikely win for Donerail means he is still the longest odds winner of the Kentucky Derby at 91.45-1, which means a $10 bet paid out $914.50 in 1913.

Matt Serra at 7-1 vs. George St. Pierre

This fight for the UFC welterweight championship took place in 2007 and very few people could see anything other than a victory for the great, GSP.

Fresh from an impressive win over one of the best welterweights ever, Matt Hughes, St. Pierre faced off against Matt Serra. Serra had been around the UFC for a while after winning Ultimate Fighter 4 but he was not supposed to pose much of a threat to Pierre in this one.

It took just moments of the fight for Serra to land a solid right hand and it wasn’t long before Pierre was on his back and tapping out with only 3 minutes and 25 seconds gone in the first round.

In an interview with Fox Sports, George St. Pierre described the night as “the biggest humiliation of my life”.

At 7-1, which is a big underdog for a championship fight in a combat sport, a $10 bet on Serra would have returned $70. Not too bad for an event that lasted just shy of 3 and a half minutes.

Warriors at 9-1 vs. Mavericks

This upset also took place back in 2007 and featured the Dallas Mavericks who were going up against the Golden State Warriors. In contrast to today, the Warriors were big underdogs and only made their way to the playoffs via a wildcard.

On the other hand, the Mavericks had cruised through the regular season with just 15 losses and 67 wins!

The teams faced off in the championship play-offs and few people saw anything other than a win for the Mavericks.

Of course, the Warriors had other ideas. This misfit team worked hard and played for each other on the court, which had the fans believing something special could happen, chanting “we believe” at their games during the season.

The Warriors took this now infamous “we believe” mantra and proved they meant it by beating the Mavericks 4-2 in the 7-game playoff series to become the first team in history seeded 8^th to beat the top seeds.

With the bookies, the Warriors were 9-1 to simply win the series but an even bigger 16-1 to take the series in 6 games. So, a $10 bet on that would have had $160 in your pocket.

Mike Tyson vs. Buster Douglas at 42-1

Whenever upsets and shocks are mentioned in boxing, it is never long before this fight is mentioned. Even today it is regarded by many as the biggest upset in heavyweight boxing history.

At the time, “iron” Mike Tyson was knocking guys out for fun and had an incredible 37-0 record with 33 knockouts.

In the other corner, stood James “Buster” Douglas with a less stellar record of 29-4-1 with 19 knockouts.

The fight was held in Tokyo on February 11^th and was supposed to be nothing more than a warm-up bout for Tyson. The undisputed champ was due to take on Evander Holfyfield who was the number 1 contender.

Unfortunately for “Iron” Mike, things did not go to plan as he was taken all the way to the 10^th round before being put on the canvas by a big right uppercut from Douglas. Famous images of Tyson putting his mouthguard in backward as the ref counts him out are etched in boxing fan’s memories.

For this fight, Douglas was a 42-1 underdog. Outrageous for a heavyweight title fight! Some casinos at the time even refused to make odds as the fight was viewed as such a foregone conclusion. A $10 bet on this one would have netted a healthy $420 on the night.

The Mets in the 1969 World Series at 100-1

In 1969, the New York Mets were going into only their 8^th season as a team in the national league. Their previous season had not ended with anything more than a 9^th placed finish. The Mets also hold the record for the most losses in the 20^th century with 102 defeats in 1962.

For these reasons, the bookies had them at 100-1 to win the World Series as they faced the Baltimore Orioles in the best-of-7-games final series. After losing game 1, the Mets rallied to a 4-1 victory in the series and claim the championship.

A $10 bet on the Mets at 100-1 paid out $1000.

The New York Giant at 100-1 vs. The Patriots – Super Bowl XLII

At Super Bowl 42 in 2008, the NFL championship was to be decided between the New York Giants and the New England Patriots.

The undefeated Patriots had been breaking records all season long as the first team in history to record a perfect 16-0 regular season. While the Giants went 10-6 and made the playoffs as a wildcard entry.

The game went to the wire with the Giants, led by MVP Eli manning, winning on their final drive of the game. Plaxico Burress completed a 13-yeard reception for the game-winning touchdown and, after a good kick, the final score was 17-14.

With the odds of the Giants being 100-1, the pay-out on a $10 bet was $1000.

The USA at 500-1 Vs. England – 1950 World Cup

England were heavy favorites for this group game of the 1950 football World Cup, which was being held in Brazil. England’s stars had an international record of 23 wins, 4 losses and 3 ties at the time.

The USA team was made of mostly part-time players and had been outscored by 45-2 in the last 7 international matches.

All of this made little difference on game day as the USA went on to win by a solitary goal scored by Haitian-born Joe Gaetjens. Such was the magnitude of this victory that it was profiled in a book, which then became a film.

The USA were 500-1 underdogs to beat the English that day so a $10 bet returned $5000.

Soviet Union Vs. The USA at 1000-1 – 1980 Olympic Ice Hockey

Famously known as “the miracle on ice” this matchup between the Soviet Union and the USA was a medal-round game played during the 1980 Winter Olympics at Lake Placid in New York.

At the time, the Soviet Union was the dominating force in the sport having won gold at 5 of the previous 6 Winter Olympic tournaments.

The USA were mostly amateur players and were the youngest team in the tournament. As a result, they were expected to get demolished by the Soviets, but it didn’t pan out that way.

The United States came back from 3-2 down to clinch a 4-3 victory over the heavy favorites before going on to win gold in their next game against Finland.

The odds of the USA defeating the Soviet Union were 1000-1, meaning a $10 bet would have returned $10,000.

Aleksandr Karelin vs. Rulon Gardner at 20000-1 – 2000 Olympic Finals

This final underdog story was a true David and Goliath story in the finals of the wrestling at the Sydney Olympics in 2000.

Karelin is regarded as the greatest wrestler ever at the time. He had not lost a single match in 15 years or a single point for the last 10 years.

He had already beaten his challenger, Gardner, 5-0 3 years before this match and was expected to dominate him again.

Gardner, who had only managed a 5^th place finish at any international contest before pulled off the shock of a lifetime to win the Olympic title and defeat a legend in the process.

Before the match, odds of Rulon Gardner conquering Karelin were an astonishing 2,000-1. This means a $10 bet would have paid out $20,000!