Most Insane Super Bowl Winning & Losing Bets

It’s that time of year again. Super Bowl LX will be here soon and that means fans and sports bettors get the opportunity to make some of the craziest bets in the industry. The Super Bowl basically created the entire props betting markets that we see today in all sports.

Bettors can wager on everything from the first song played by the halftime entertainment to the color of the Gatorade that will be poured on the winning head coach at the end of the game. Even with all the outlandish wagers, most Super Bowl bets will still be on the moneyline, point spread, and game total.

Whatever you choose to bet on in Super Bowl 60, hopefully you’ll win like some of these crazy winners and not lose like some of these bad beats. Here’s a look at some of the most insane winning and losing Super Bowl bets of all-time.

Mattress Mack Strikes Again

If you don’t know Mattress Mack, aka Jim McIngvale, click here to read more about him. The guy owns a chain of furniture stores, and he is known for his crazy sales promotions and his affinity for betting on sports.

In 2022, Mattress Mack bet $4.5 million on the Cincinnati Bengals to win Super Bowl LVI. That, of course, was a loser, but that bet did set a record for the largest mobile wager in history. Mack brushed off that loss, by the way, when he won $75 million betting on his own Houston Astros to win the 2022 World Series.

Prior to his wager on Super Bowl LVI, Mack bet $3.46 million on Tom Brady and the Tampa Bay Buccaneers to win. They did and Mack won $6.18 million, which was used to hedge one of his sales promotions.

The Almost Cross Sport Parlay

Cross-sport parlays are not only fun, but they can produce some big wins. A sports bettor named Wayne Shelton put $100 on a simple three-leg parlay in May 2023. Shelton bet on the Texas Rangers to win that season’s World Series. They did.

He also included a Super Bowl leg in that parlay. Shelton picked the Kansas City Chiefs to win Super Bowl LVIII, which they did. The Chiefs won in overtime when Mahomes threw a touchdown pass for the win. 

The final leg of the parlay was the Oklahoma City Thunder to win the NBA title. As we now know, Shelton was a year too early. However, in the 2023-24 NBA playoffs, the Thunder fell behind Dallas 2-0 in the series. It was at that point, Shelton decided to cash out on a chance to win $1.7 million. 

Instead, he pocketed $80,000. It was a smart play. The Thunder lost to Dallas in that series. Boston would go on to win the NBA title.

Crazy Prop Bets

There have been a number of wild Super Bowl prop bets that have ended up being very productive for bettors. In 2022 at Super Bowl LVI, a number of sportsbooks offered odds on whether or not an on-field marriage proposal would take place. 

The odds weren’t outrageous at +400 at BetOnline and a number of bettors quadrupled their stake when Los Angeles Rams safety Taylor Rapp dropped down on one knee after the game ended and proposed to his high school sweetheart Dani Johnson.

Another wild prop that cashed for bettors in Super Bowl LVII was the “doink” bet. The Yes/No wager would pay out if either kicker hit one of the crossbars on a field goal or extra point attempt. At odds of +1400, the “doink” had roughly a seven percent chance of cashing. 

Sure enough, Chiefs kicker Harrison Butker cashed that one early. He hit the upright on a 42-yard field goal attempt in the first quarter.

He Only Needed One

Speaking of Butker … it seemed like a sure bet. Just last year, one Super Bowl LIX bettor wagered $2200 on the Kansas City kicker to make at least one extra point. Butker had gone 29 for 31 on extra points during the season and he hit at least one in every game but one. That game happened to be the regular season finale when none of the Chiefs starters played. 

If you recall, the Philadelphia Eagles got off to a great start, leading 34-0 late in the third quarter. QB Patrick Mahomes would lead the Chiefs to a late third quarter touchdown, but head coach Andy Reid elected to go for two. 

Kansas City would end up scoring twice more, but Reid opted for two-point conversion tries after both touchdowns. Butker ended the game with zero PAT attempts and zero field goal attempts.

Don’t Call It a Comeback

Imagine placing a $1.1 million bet on your team to win the Super Bowl. Then, they jump out to a seemingly insurmountable 28-3 lead late in the third quarter. The opponent finally scores a touchdown with about two minutes left in the third quarter but misses the extra point! 

The year, of course, was 2017 and it was Super Bowl LI. The Atlanta Falcons held that big lead before Brady and Patriots would score 25 unanswered points to force the first-ever overtime in Super Bowl history.

The Patriots would take the overtime kickoff, drive 75 yards in eight plays, and win 34-28 after a two-yard TD run by James White. It was the biggest comeback in Super Bowl history and also cost one bettor $1.1 million.

At It Already

With New England and Seattle set to face each other in Super Bowl LX, the betting markets are open and bettors are at it already. One bettor, who already won $1.4 million on the Seahawks after they clinched the NFC title, reportedly has another wager on the Seahawks to win the Super Bowl. That bet would pay out $4.5 million!

BetOnline has reportedly already taken a massive bet on the Patriots to win it all. A bettor has placed $1.1 million on New England at moneyline odds of +188. If the Patriots win, the bettor would win roughly $2.1 million!