March Madness is arguably the best event in basketball—bar none. Millions of people who ignore the sport for eleven months out of the year tune in for three weeks to watch the best collegiate athletes on the planet duke it out for the brass ring.
Millions of dollars in bets trade hands as people make brackets and cheer on their favorite teams.
If your team has entered the tournament as a low seed, you’re naturally hoping for an upset. Historically speaking, those can be hard to come by in March Madness.
Betting every underdog in March Madness is fun, and can pay well if you get lucky, but the odds are long for a reason. What are the best underdog stories in March Madness? Let’s take a look.
First: How Does The Tournament Work?
The sixty-four best college teams in the country enter the tournament in mid-March. Each round is single-game elimination. Lose once, you are out. It’s this component that adds a spicy volatility to the tournament.
In basketball, almost any team can be brilliant for a night. The field of sixty-four is reduced to sixteen, then to eight, then to four, until we reach the Finals.
During each stage, the top seed is pitted against the bottom seed. This gives top-ranked teams a relatively easy path to the Elite Eight while making it very difficult for “underdogs,” to advance.
Though March Madness has been around for nearly one hundred years, the format described above wasn’t adapted until 1985. For that reason, outcomes prior to that date are generally regarded with a sort of asterisk.
Even before the more mature playoff template that we now use, March Madness upsets were pretty rare. Across sports, post-season play generally highlights this complicated truth: There is a big difference between good teams and great teams.
Biggest March Madness Upsets
Here’s a little secret: March Madness doesn’t really have many big upsets. There are small ones, sure. Every tournament a little team in the top 64 bracket will knock out a different little team in the top 64 bracket. By the time we get to the Sweet Sixteen, most outcomes stick to the script.
Why? Well, for one thing, it’s at this stage of the event that major mismatches take place. The sixteenth team is pitted against the first team. Virtually every time, the bottom-ranked school’s story ends there.
Only twice in the history of the tournament has a 16th seed knocked the top-ranked team out of the tournament. Interestingly, both of these upsets were relatively recent.
It happened first in 2018 when a strong Virginia team began their March campaign with a stacked lineup. The Virginia boy’s team was expected to win the entire tournament. Unfortunately for them, those ambitions were extinguished early when they went head to head with the sixteenth seed, UMBC.
Not only did Virginia lose, but they lost spectacularly in a 74-54 contest. Virginia would make things right the following year, winning the entire tournament.
The second major upset happened in 2023. “The more I watch Purdue, the more I think we can beat them,” said Fairleigh Dickenson Coach Tobin Anderson.
Well, he was right. It was a close, two-possession game in which National College Player of the Year put up 21 points for Purdue. It simply wasn’t enough. Fairleigh Dickenson won, 63-58 before losing to Florida Atlantic in the next round.
Does the recency of these upsets say something about the future of the game? It’s possible. College sports have changed a lot in the last decade or so. While there has always been roster volatility—players graduating or going pro—lineups change now more than ever. Roughly 25% of scholarship-level college athletes changed schools after the 2023 season.
Not only does this fluctuating environment create challenges for coaches, but it might also change the way we understand the game.
Throw in the incredible amount of data that modern teams use to make their decisions and a heaping handful of luck, and what do you get? Three weeks of postseason play in which anything at least feels possible.
Are There Any Likely Upsets This Season?
The very nature of an upset is that they are unlikely. Generally, when they do happen, they are pretty small occurrences. One low-ranked team taking out another relatively low-ranked team. If you are making a bracket, it’s not sensible to plan for more than 6-8 small underdog triumphs.
The most salient figure for sports bettors: The top five ranked teams going into March Madness win virtually 100% of the championships.
Now, if you and your spouse are sitting down at the kitchen table to make a competitive but un-staked bracket, it’s ok to get a little fanciful and predict with your heart rather than your brain. You’ll probably lose but go right ahead.
If money is on the line, get smart.
You can watch the game as a fan but bet as a person with bills to pay. You don’t wager on your favorite team. You stake the one most likely to win.
