The 10 Biggest Longshot Wins In Sports Betting History

With Loyola-Chicago narrowly losing out on being the NCAA Tournament’s greatest longshot to win a championship, everyone must be wondering, “Who are the biggest longshots in sports betting history?”

Lucky for you, this article is all about the 5 biggest Longshot wins in sports betting history we collected together with gambling experts from Casinomech. Longshots aren’t all made equal. Some of these choices were no-brainers, permanently engraved in gaming history. Others were a bit more under-the-radar, but they were nonetheless noteworthy.

5. 2011 St. Louis Cardinals at 999-1

The St. Louis Cardinals were 4 ½ games behind the Atlanta Braves for the National League wild-card position with 15 games remaining in the 2011 season. They were 999-1 to win the World Series at Las Vegas bookies. After Atlanta’s collapse, the Cardinals went 11-4 in their last 15 games and defeated the Texas Rangers in the World Series. While it takes a lot to keep baseball fresh and thrilling, a 999-1 run does the trick.

4. 1999 St. Louis Rams 300-1 to Win Super Bowl

Let’s keep the list in St. Louis for the time being. While some may believe that the 2001 Patriots had the lowest preseason Super Bowl odds, they were really 60 to 1 and just the fifth worst preseason Super Bowl odds to win the Lombardi Trophy. The St. Louis Rams, who they defeated in the Super Bowl that year, claim the title of greatest pre-season Super Bowl longshot to win it all.

To put things in perspective, the Rams of the late 1990s were terrible. Awful. As Charles Barkley would say, “terrible.” Trent Green, their top free-agent quarterback signing, sustained a season-ending injury before the start of the season, so Kurt Warner, a grocery bagger, took over. What happened after that? The Greatest Show on Turf and a Super Bowl that may or may not happen.

3. Buster Douglas at 42-1 Kos Mike Tyson

We’re entering rarefied air now.

By any measure, Buster Douglas’ win against Mike Tyson in Tokyo, Japan, in 1990 was far from the most unlikely. That does not seem to be the case anymore.

Douglas was an unheralded bystander. Mike Tyson was Mike Fucking Tyson. He has a record of 37-0 with 33 knockouts. This is what he did to other heavyweights.

Buster Douglas was almost 7 years older than Tyson and had 4 more defeats. Regardless, after being knocked down in the eighth round, Buster recovered and ended Tyson’s reign with a knockout in the tenth round. Tyson’s career as a boxer was cut short. After losing his next bout against Evander Holyfield, Douglas was no longer relevant.

2. Leicester City 5,000-1 to Win 2015 Premier League

Leicester City, a chronic relegation contender, began as 2,000-to-1 to 5,000-to-1 underdogs to finish first in the Premier League before the start of the 2015 season. Leicester won the Premier League for the first time in a strange season that saw traditional favorites Manchester United, Liverpool, and Chelsea finish 5th, 8th, and 10th, respectively. Leicester City, for example, has never won the Premier League. Nonetheless, they did.

Thousands-to-1 bettors who backed the Foxes were ecstatic, much like Zlatan Ibrahimovic after his first MLS goal.

1. New York Jets +18 Super Bowl III

It’s important to remember that it’s not always about the spread. While being an 18-point underdog is significant, the impact that Joe Namath’s guarantee and the New York Jets Super Bowl victory had on the NFL and the Super Bowl, in general, makes this longshot much more significant.

Would the NFL have remained the most popular sport in the United States? Absolutely. Would legalizing sports betting help them boost their ratings? Once again, absolutely! But did Namath’s promise and iconic field walk-off gesture of dropping the mike #1 help speed up the process? Maybe.