Biggest Betting Wins and Losses in March Madness History

March Madness Tip Off

NCAA Slam Dunk

photo credit Bob Donnan-USA TODAY Sports

March Madness, the NCAA Men’s Division I Basketball Tournament, draws significant attention to the sport and the betting it inspires. This period sees wide participation across the United States, where individuals engage in various forms of betting, from casual pools among friends to more formal bets online. As this event unfolds, it's accompanied by a surge in betting activity, reflecting the broader trends in the nation's growing acceptance and regulation of sports betting. 

Record-Breaking March Madness Bets

In 2023, the American Gaming Association (AGA) reported that an estimated 68 million Americans, equating to a quarter of all adult Americans, planned to wager a total of $15.5 billion on the NCAA Men’s Division I Basketball Tournament. This betting enthusiasm was split across the most popular U.S. Sportsbooks, with 31 million Americans engaging in traditional sports wagers online, at retail sportsbooks, or through bookies. Additionally, 21.5 million were expected to bet casually with friends, and 56.3 million aimed to participate in bracket contests. The surge in betting was attributed to the growth of legal online wagering options and a resurgence of interest in bracket contests, with three-fourths of online bettors participating in March Madness betting for the first time. This period marked the first time the tournament featured Las Vegas as a regional host location, underscoring the expansion of regulated sports betting and its integration into popular sports traditions​​.

So what does this mean for March Madness 2024? 

While the AGA has not released specific projections, it's reasonable to anticipate an increase in both participation and the amount wagered, given the trends in legal sports betting and the tournament's growing popularity. 

Biggest Betting Wins at March Madness

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

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."

How $33k Became $495k on a Longshot


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. 

Biggest Betting Losses at March Madness

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. 

Losing March Madness Ticket

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.

Biggest Bonus Offers for March Madness

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.

Bonuses for March Madness

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Final Thoughts

As we reflect on March Madness, it's evident that the tournament is not just a showcase of collegiate athletic talent but also a significant event in the sports betting world. 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.

FAQs Biggest Wins/Losses on March Madness

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Meet Our Authors

Sol Fayerman-Hansen
Sol Fayerman-Hansen

Sol's interest in sports was sparked at a young age, inspired by athletes such as Barry Sanders, Michael Jordan, and Wayne Gretzky. This early fascination evolved into a deep-seated passion, guiding him toward a career in sports journalism in 2007. Over the years, Sol has contributed numerous articles and reviews to various online platforms, sharing his knowledge and perspectives.

Central to Sol's approach is his dedication to honesty, especially regarding sports betting platforms. He believes in providing bettors with straightforward and detailed reviews, distinguishing his work by avoiding the often overly positive spin on bonus offers and promotions. His commitment to truthfulness has made his reviews a reliable source for those seeking authentic advice and information, thereby earning him a reputation for integrity among his readers.

“In the world of sports betting, truth is more valuable than any bonus offer.”

Content Manager, OnlineCasinoReports2012-2021
Sports Journalist, Dottraffic2009-2011
Content Writer, HouseTech2007-2009
Cristina Varela Galan
Cristina Varela Galan
Problem Gambling Expert

Cristina used to work as a Psychology Assistant in the Bizkaia Pathological and Risky Gamblers Association. She was also part of a research team in Deusto University, specializing in pathological gambling area. While working there, she managed to develop her own project 

 “Exploring the association between emotional regulation, alexithymia, stressful life events and gambling in adolescent and young adult women”.

Paruyr Shahbazyan began his business career in 2000 as a private entrepreneur. Over thirteen years, he developed a deep understanding for business and leadership, laying a solid foundation for his professional journey.

In 2013, Paruyr stepped into the sports and betting industry as the founder and president of Bookmaker Rating. This online mass media platform, which he led until 2020, focused on providing in-depth analysis and insights in sports betting, earning a reputation for its quality content. 

Continuing his innovative approach in 2022, Paruyr co-founded Azuro, a decentralized betting protocol. This venture showcases his dedication to integrating advanced technology in the evolving landscape of sports betting. Through these diverse experiences, Paruyr has continuously influenced and shaped the betting industry, driving new trends and setting high standards.

Engaged in private entrepreneurship2000-2013
Founder and President at Bookmaker Rating, an online platform focused on sports and betting2013-2020
Co-founder at Azuro, a decentralized betting protocol2022

"Innovation in sportsbetting comes from a deep understanding of both technology and the human element of sports." 

- Paruyr Shahbazyan, Founder, RG


Principles and Ethics

Paruyr Shahbazyan's core beliefs lie in the power of informed decision-making and integrity in the betting industry. He understands that the foundation of successful betting is not just about odds and predictions, but also about the trust and reliability of the information provided. Paruyr advocates for a betting environment where transparency and knowledge are paramount, ensuring that bettors are well-equipped with accurate data and insights.

Strategic Vision

Paruyr's vision is to revolutionize the sports betting industry through the integration of technology. He sees the future of betting as a blend of traditional sports knowledge with innovative tech solutions, like decentralized protocols, to enhance user experience and fairness. His aim is to create platforms that are not only user-friendly but also uphold the highest standards of ethical betting, contributing to a more responsible and enjoyable betting culture.

Future Perspectives

Looking towards the future, Paruyr envisions a betting landscape that is more inclusive, technologically advanced, and globally connected. He anticipates a significant shift towards more decentralized and transparent betting systems, driven by blockchain technology. Paruyr is committed to being at the forefront of this change, continuously exploring new possibilities and innovations that can redefine what it means to engage in sports betting in a digital world. His focus is on building systems that prioritize user empowerment, fairness, and the global growth of the sports betting community.


Anna Kravtcova
Anna Kravtcova
Problem Gambling Expert

Ph.D. in organizational psychology, an internationally certified psychologist (EuroPsy 2022, Cognitive behavioural therapy of mindfulness 2020, International Society for Emotional Intelligence 2017, Russian Psychological society 2014, American Psychological Association(Society for Industrial and Organizational Psychologist) 2011), speaker of many international conferences (USA, Brazil, Portugal, Czech Republic, Russia, etc.). TEDx speaker.

Mike Rosenberg
Mike Rosenberg
Content Writer

Mike made the decision to dive headfirst into the booming world of sports betting fresh out of college. Back in the day, when 1-800 pick lines and sports pagers were all the rage, he couldn't resist the allure, having grown up idolizing sports legends like Sweetness, MJ, and Slammin Sammy. Mike dedicated his early years to the industry, tirelessly analyzing games, writing articles with free picks, and selling his expertise on reputable handicapping sites. Unlike many others, Mike was known for his integrity and only released one Game of the Year per sport, per season. His hard work and unwavering commitment paid off, earning him a devoted following and propelling his career to new heights. Then came the explosion of Daily Fantasy Sports. Believe it or not, companies like DraftKings and FanDuel used to pay Mike's company to increase their brand exposure. Now, those same industry giants don't even bother responding to his emails. While Mike appreciates the convenience of being able to place legal bets in his own backyard, he can't help but feel disheartened by what has become of the industry. People are being led astray, falsely believing that a mere $5 wager on a 20-team same-game-parlay will be their ticket to financial security. If there’s one thing Mike learned from making book back in the day, it’s that parlays are a bookie’s best friend. A bankroll is the only leg you have to stand on in the battle with the books, and Mike’s here to offer up advice on how to protect it.