The Biggest Wagers in Sports History: Legendary Bets and Their Outcomes

The Biggest Wagers in Sports History: Legendary Bets and Their Outcomes

The Biggest Wagers in Sports History: Legendary Bets and Their Outcomes 1125 750 The Ultimate Lineup

As we like to say here at Xam Sports Consulting, sports betting is a business filled with the highest of highs and lowest of lows. Well, it doesn’t get much bigger than some of the biggest sports bets in history! Keeping your emotions in check as a sports investor is the most important thing you can do, but it’s hard to be levelheaded when you have millions of dollars on the line. Check out some of the biggest wagers in history and the results of these wagers:

1. Floyd Mayweather’s Super Bowl Bet

Event: Super Bowl XLVIII (2014)
Wager: $13 million
Outcome: Lost

Floyd “Money” Mayweather, known for his extravagant lifestyle and high-stakes bets, placed a massive $13 million wager on the Denver Broncos to win Super Bowl XLVIII against the Seattle Seahawks. Unfortunately for Mayweather, the Broncos were crushed by the Seahawks, losing 43-8. This significant loss was just one of many high-profile bets placed by the boxing superstar.

2. Anonymous Bettor’s World Series Win

Event: 2017 World Series
Wager: $14 million
Outcome: Won

An anonymous bettor made headlines by placing a series of bets on the Houston Astros to win the 2017 World Series. The bets, which were placed in Las Vegas, totaled around $14 million. The Astros triumphed over the Los Angeles Dodgers in a thrilling seven-game series, securing the anonymous bettor a substantial payout estimated to be around $10 million.

3. Billy Walters’ Super Bowl Bet

Event: Super Bowl XLIV (2010)
Wager: $3.5 million
Outcome: Won

Legendary sports bettor Billy Walters placed a $3.5 million bet on the New Orleans Saints to cover the spread against the Indianapolis Colts in Super Bowl XLIV. The Saints, considered underdogs, won the game 31-17, resulting in a significant windfall for Walters. This bet is one of many that contributed to Walters’ reputation as one of the most successful sports gamblers in history.

4. Mattress Mack’s Astros Bet

Event: 2019 World Series
Wager: $11 million
Outcome: Lost

Jim “Mattress Mack” McIngvale, a Houston furniture store owner, placed several bets totaling $11 million on the Houston Astros to win the 2019 World Series. McIngvale’s bets were part of a promotion offering customers free mattresses if the Astros won. Unfortunately, the Astros lost to the Washington Nationals in seven games, resulting in a substantial financial hit for McIngvale.

5. Charles Barkley’s Super Bowl Bet

Event: Super Bowl XXXVI (2002)
Wager: $500,000
Outcome: Won

NBA legend Charles Barkley placed a $500,000 bet on the New England Patriots to win Super Bowl XXXVI against the heavily favored St. Louis Rams. The Patriots won the game 20-17, thanks to a last-minute field goal by Adam Vinatieri. Barkley’s bold bet paid off handsomely, adding to his already impressive wealth.

6. Phil Mickelson’s Baltimore Ravens Bet

Event: Super Bowl XXXV (2001)
Wager: $20,000
Outcome: Won

Golf legend Phil Mickelson placed a $20,000 futures bet on the Baltimore Ravens to win Super Bowl XXXV at 22-to-1 odds. The Ravens dominated the New York Giants, winning 34-7, and Mickelson walked away with $560,000. This successful wager is one of the few public bets known to be placed by Mickelson, who is rumored to have a penchant for gambling.


Needless to say, these bets don’t represent the money management and discipline that we preach! However, it just goes to show that this is a high stakes game, and you have to be mature enough to handle a loss. If you can handle a loss with maturity, regardless of the amount bet, you’ll be in a better position to win your next bet and have more fun doing it.