Editor’s Note: This is a guest post from PoolGenius, the leader in data-driven NCAA bracket strategy. Since 2017, they have helped subscribers win $2.5 million in bracket pools, winning at 3.1 times the expected rate.
March Madness is known for its chaos, and every year, fans fill out their brackets, hoping to nail the perfect Cinderella story. But picking too many upsets can quietly sink your bracket before the first weekend ends.
While some upsets are inevitable, overloading on them is a common mistake that costs casual players year after year. So how many upsets should you pick in your bracket? When should you play it safe or roll the dice?
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It’s called March Madness for a reason. Underdogs make headlines, buzzer-beaters go viral, and every fan dreams of calling the next Loyola-Chicago or Saint Peter’s run. The problem? Most of these deep Cinderella stories are nearly impossible to predict in advance.
Sports media feeds into this excitement, with analysts hyping potential bracket-busting teams every March. While picking the right Cinderella team is fun, blindly choosing multiple upsets can be a death sentence in a standard bracket pool—especially smaller ones with fewer than 50 people.
There’s no universal rule on how many upsets to pick, but history shows that most players pick too many. Data from past NCAA Tournaments suggests that being more conservative with early-round upsets leads to better results.
The key is to choose your spots, with intelligent value picks where the odds are only a little more risky than the top alternative, and you are getting a popularity discount, rather than scattering risky upset picks all over your bracket.
Take the classic 12-over-5 seed upset, for example. It happens roughly 30% of the time, about one per year in a typical tournament. Yet, the public consistently picks too many 12-seeds on average, well above the historical rate.
If you randomly select one 12-seed to win, your expected points scored are 2.5 on average. But if you simply take all four 5-seeds, your expected score jumps to 3.0—a 20% increase.
That doesn’t mean you should never pick an upset, but only when the data and matchups support it. Instead of filling out your bracket with many upsets just because you feel like there will be surprises, focus on making calculated risks based on team strength, matchups, and public perception.
But what about the years when the brackets get wrecked by upsets? We saw this in 2018 when Loyola-Chicago, a No. 11 seed, made a Final Four run. On the left side of the bracket, two No. 9 seeds, two No. 7 seeds, and an 11-seed advanced past the first weekend.
We also saw extreme upsets in 2021 when none of the No. 1 seeds made it past the Sweet 16. The Final Four consisted of a No. 4 seed (Connecticut), two No. 5 seeds (Miami and San Diego State), and a No. 9 seed (Florida Atlantic).
As it turns out, the “don’t get too crazy with upsets approach” worked fine those years. Our subscribers reported winning pools 3.8 times more often than expected in 2018.
In 2023, it was 2.7 times more often than expected, but a higher percentage of those wins came in larger pools, where Connecticut was one of our key value champion picks as an underpicked No. 4 seed to win the title.
The truth is that most entries do not pick upsets like “Loyola-Chicago to the Final Four,” and an even smaller subset has “Villanova as national champion, plus Loyola-Chicago to the Final Four.”
Even in those chaotic years, the public was not good at picking the right upsets. Our data shows that in 2018, the public averaged 21.6 first-round wins, while a more disciplined approach averaged 23.9.
In 2023, the public average had 21.7 first-round wins, and our picks had 23.7. By being selective rather than reckless, smart brackets stayed ahead of the pack even in an upset-heavy year.
While a conservative approach works best in most standard pools, exceptions exist. The strategy changes if you’re in a large pool (several hundred entries, or where fewer than 1% of entries finish in the money) or a pool that gives bonus points for upsets.
In those cases, a more aggressive risk-taking approach may be necessary to separate from the crowd.
For example, picking more upsets could be beneficial if your pool awards extra points based on seed difference (e.g., a No. 12 beating a No. 5 earns 8 points instead of 1 point). But even then, it’s about smart risk allocation—not just picking upsets for the sake of it.
The biggest mistake people make in bracket pools is picking too many upsets. A disciplined approach—selecting a few well-researched upsets while sticking with favorites—wins far more often than blindly chasing Cinderella stories.
Playing it safe and letting others make mistakes is often the smartest move if you’re in a smaller pool. In larger pools, you can take more risks, but it should always be calculated.
Upsets will happen, but knowing when to pick them is more complicated than it seems. Be strategic, pick your spots, and don’t let the upset bug sink your bracket before the Sweet 16.
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