Biggest Betting Wins and Losses in March Madness History

Over the years there have been many big March Madness wins among U.S. bettors. More often than not, the house is the winner but some bettors have made the headlines with their bets.

One of the biggest longshot bets in history was made during the 2021 March Madness tournament by Colorado native Eli Sawaged, who placed a $10 bet on a 10-team parlay and incredibly took home over $33,000. This was the biggest longshot bet ever won in March Madness history. 

Eli Sawaged (credit: CBS)

Sawaged needed Oregon State to win over Oklahoma State to complete his Parlay Bet. Leading up to the game, he could have taken $22,000 as an Early Cashout offer at DraftKings Sportsbook, where he made his bet, but instead, he let the bet ride.

"I fully went in expecting to lose that $10," he told CBS News in their interview with him. "I've never been an Oregon State fan, but I'm debating getting a tattoo or something because they came through for me. Nobody in my family has ever been an Oregon State fan, but we all are Oregon State fans now."

Photo credit: Paul Sancya/AP

In last year’s March Madness, we saw a major upset when 16th-seeded Fairleigh Dickinson Knights upset No. 1 Purdue. Obviously props to the the Knights for pulling off one of the biggest upsets in March Madness history, but it also gave way for one of the biggest bet wins as well. A bettor placed a $33,000 bet on Fairleigh Dickinson to win outright, which resulted in $495,000 at DraftKings Sportsbook. 

Now, this type of bet was probably made by someone who can afford to spend $33,000 on a wager, but let’s face it, taking home close to half a million dollars would be a very good day for anyone. 

Unfortunately for sports bettors everywhere, there are a lot more losses than there are wins during the NCAA Division I Championship. Over the years there have been many users who have posted their losses on social media, but few have lost like one bettor who went in big on Princeton in 2023. 

The bet, made at Beau Rivage Resort and Casino in Biloxi, Mississippi, amounted to $344,126 on a parlay involving Missouri and Alabama. Despite Alabama's win over Maryland, Princeton's upset over Missouri meant the bet did not pay off. Princeton's performance, highlighted by Blake Peters' five 3-pointers, showcased their prowess in the 2023 tournament, leading to an unexpected victory.

This type of bet should only be practiced if this is part of one’s affordable bankroll and for that to happen one should be earning 10x that amount to be making this bet responsibly.

During March Madness, fans engage in various betting formats, with bracket contests, point spreads, and over/under bets leading in popularity. The appeal of betting on underdogs for potential large payouts versus choosing top-seeded teams for a perceived safer bet illustrates the diverse strategies within the tournament.

Futures bets are typically the most popular bets made before the tournament and up until the First Round, but there is always a lot of volume for Live In-Play Betting, Parlay Bets, and bettors trying the longer shots offered on Odds Boost markets. Check out our March Madness Odds Analysis on all the teams that are competing this year to help you make a more informed decision. 

Basically, all U.S. sportsbooks provide odds on all of the games at March Madness but following our research, the most popular U.S. sportsbooks include DraftKings, FanDuel, BetMGM, bet365, and newcomers ESPN BET. They are favored for their range of betting options, interfaces, and comprehensive event coverage. 

Online sportsbooks present bonus offers throughout the year and most can be applied to March Madness, including welcome bonuses, parlay bonuses, odds boost promotions, among others. Some Sportsbooks, like Bet365 have gone a bit further by providing unique offers on the tournament with the Bet365 NCAAB Early Payout bonus.

The American Gaming Association's report highlights the vast participation and financial engagement among Americans, hinting at the broader acceptance and integration of sports betting into our cultural fabric. The tournament's unpredictable nature is encapsulated in the stories of unprecedented wins and losses, reminding us of the high stakes involved. While the excitement of betting can enhance the experience, it's crucial to approach gambling with caution and responsibility, recognizing it as a form of entertainment rather than a guaranteed income source. As the legal landscape evolves, and participation grows, remembering the fundamental principle of betting within one's means remains paramount.