March Madness Betting: A History Of Wagers & Upsets

Bodog unpacks the history of wagers and upsets for March Madness – dive in to read the most memorable moments.

Apart from the obvious entertainment, the NCAA division’s March Madness basketball tournament provides a fantastic opportunity for basketball fans to see fresh new talent showcasing their skills, knowing that this is their moment to shine. It’s a glimpse into the NBA’s next generation of stars in the seasons to come. It’s also where you’ll see some of the most exciting and unpredictable matches ever played.

As a single-elimination competition, the outcomes are always unpredictable, which is a dominant reason why betting during March Madness is so popular. Unpredictability, after all, keeps us on our toes.

The Biggest Upsets in March Madness History

Every year, fans and punters collectively spend around $9 billion in March Madness betting, though few throw down quite as much as high rollers like Mattress Mack.

In last year’s tournament, the businessman reportedly placed a $1 million futures bet on the University of Houston in a Texas-sized show of support for his hometown.

This bet eclipsed the $100K Derek J. Stevens, the owner of a Vegas casino, placed on Duke, Gonzaga, Michigan, and Kansas back in 2019. In both cases, the teams had good odds and were looking strong, but March Madness upsets led to both bettors kissing their wagers goodbye. Presumably, Mack still had a mattress to commiserate on that night, and Stevens had… well, a casino. Hold the GoFundMe.

However, in 2021, Eli Sawaged, a pharmacy technician in Colorado, enjoyed a different fate. He turned a $10 wager into $33,000 by picking a mix of underdogs and favourites in a parlay.

Another anonymous bettor pulled off a five-team parlay to pocket more than $11,000 from a $65 wager by backing Maryland, Ohio, UCLA, Oklahoma, and Abilene Christian.

Biggest Shocks In March Madness History

Back home at Bodog Casino, we’re feeling the excitement as this year’s NCAA Tournament imminent, and accordingly we’ve decided to dig into the history of March Madness betting and highlight some of the biggest upsets thrown up by this competition that lives up to its name.

Villanova vs Georgetown – 1985 National Championship

Georgetown were the 1984 March Madness winners, and had been the favourites to do it all again the following year. A brave few would have bet against them. They were at the helm of soon-to-be NBA star, Patrick Ewing, along with the best defence in college basketball.

The Villanova Wildcats, on the other hand, were David to the Hoyas’ Goliath, despite already pulling off several notable coups by beating top-ranked teams Michigan, Memphis, and North Carolina to make it through to the National Championship game.

As the match got underway, Georgetown dominated. Had in-play March Madness betting been around then, most people would have been cashing out their Villanova wagers early on. But then when the second half came, the Wildcats turned the tables, missing just one of their many shots to clinch a 66-64 victory.

UMBC vs Virginia – 2018

Although it had less riding on it than the 1985 National Championship match, this first-round game may be a little fresher in your mind. Virginia showed up as the 20.5-point favourites, expecting to play in a one-sided game.

They were partially right; only the scales were tipped very much in the other direction, as UMBC trounced Virginia by 20 points. Those who bet on the underdog managed to cover the spread by a whopping 41 points, making it one of the biggest in March Madness history.

On only two other occasions had the number-one seed lost their first game of the tournament, but Virginia set a new record for the most spectacular flop in the opening weekend.

George Mason vs Connecticut – 2006

In 2006, George Mason faced off against Connecticut in the Elite Eight round. Considering they had just made it into the NCAA Tournament by a whisker that year, securing a place in the final eight was already an impressive achievement for the Patriots.

Connecticut, on the other hand, were the clear favourites for the tournament and therefore, naturally, the game. Things didn’t play out that way, of course, and the two sides played call-and-answer basketball as though the stats and the pundits had no serious role in the prediction business. Future minor league player Jai Lewis managed to get one over on future first-round NBA draft pick, Rudy Gay, to push the game into overtime and before finishing it at 86-84.

The story of George Mason was one that an entire nation could get behind as they charged through the competition… though Florida must have missed that memo, because the Gators made mincemeat of the Patriots in the Final Four.

Florida Gulf Coast vs Georgetown – 2013

First-round upsets are par for the course during March Madness, and 2013 gave us one of the most memorable such events in tournament history. Going into the competition, Georgetown were the number-two seed, while Florida Gulf Coast were down and out in 15th place. Not only that, but the underdogs were only competing in the NCAA Tournament for the third time in their team’s history, which is less surprising when considering they were founded in 1997.

Florida Gulf Coast started this unexpected Cinderella run in spectacular fashion by demolishing Georgetown 78-68. The Eagles were unofficially nicknamed ‘Dunk City’ at the time, and this game was demonstrably a case in point. After making short work of the Hoyas, FGCU managed to get into the Sweet Sixteen after knocking out San Diego.

Cleveland State vs Indiana Hoosiers – 1986

Indiana won the March Madness tournament in 1981, and again in 1987, but sandwiched between these two victorious seasons was the embarrassing first-round defeat to Cleveland State in 1986. The Hoosiers were the number-three seed that year, so of course they hit the court as strong favourites against a team ranked well below them in 14th.

Yet, another script was well and truly thrown out in this game. While future second-round NBA draft pick Steve Alford was a key asset on court, he was not a one-man army, and it showed in this game. The shock 83-77 defeat was, perhaps, the necessary evil that led to Indiana’s 1987 National Championship victory, assuming that without the move to recruit top talents Dean Garrett and Kevin Smart, the Hoosiers might’ve lost their mojo for good.

Upsets are part of the NCAA Tournament fabric, and who would have it any other way? Predicting these unexpected underdog victories from the sidelines is half the thrill, so if you think a heavy favourite is about to be toppled in devastating fashion, make sure your March Madness betting slips are signed, sealed and ultimately deliver you outsized rewards after the fireworks.