Mastering March Madness: How Many Upsets Should You Pick?

NCAA Bracket Strategy: Picking Smart Upsets Is Key

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 lives up to its name every year, delivering stunning upsets and Cinderella stories that captivate fans. But while these moments make for great headlines, they can also quietly ruin your bracket if you rely too heavily on picking underdogs.

Casual players often make the same mistake: picking too many upsets. While some surprise wins are inevitable, a disciplined approach to selecting them can dramatically improve your chances of winning your pool. So how do you strike the right balance?

The Data-Driven Approach to Bracket Success

At PoolGenius, we’ve studied NCAA bracket pools extensively, analyzing data from over 19,000 real-world contests to determine the best strategies. Our approach isn’t based on gut feelings or following the latest media hype—it’s grounded in statistical modeling and tournament trends.

The results speak for themselves:

• Our subscribers have won $2.5 million in bracket pools since 2017.
• Last year, 61% of our users finished in the money.
• Our top bracket recommendations have outperformed the public average in 37 of the last 42 rounds of the tournament.

If you want expert insights to build a winning bracket, check out PoolGenius:

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The Problem With Picking Too Many Upsets

Underdogs are fun to root for, but predicting which ones will make a deep run is extremely difficult. Every year, sports analysts and fans highlight potential bracket-busters, fueling the temptation to pick multiple upsets.

But historical data suggests that most players overdo it—especially in smaller pools with fewer than 50 entrants. A bracket loaded with risky upset picks can sink your chances before the first weekend even ends.

A smarter approach? Be selective. Instead of taking long-shot upsets all over your bracket, focus on situations where the risk is reasonable and the reward justifies the gamble.

A Smarter Way to Pick Upsets

Let’s take the well-known 12-over-5 seed upset as an example. This upset occurs about 30% of the time—roughly once per tournament. Yet the public consistently picks more than one 12-seed to win each year, which lowers their expected score.

Consider this simple math:

• If you randomly pick one No. 12 seed to win, you’ll average 2.5 points per year.
• If you take all four No. 5 seeds to win, your expected score jumps to 3.0 points—a 20% increase in expected value.

That doesn’t mean you should avoid upsets altogether. It means you should be strategic—choosing the right moments where a lower seed has a legitimate chance and is less popular than it should be.

What About Upset-Heavy Years?

Sometimes, the tournament produces extreme chaos. In 2018, Loyola-Chicago (No. 11 seed) reached the Final Four, and multiple lower seeds made deep runs. In 2021, none of the No. 1 seeds reached the Elite Eight, leading to a Final Four that included a No. 4, two No. 5s, and a No. 9 seed.

So, does this mean an upset-heavy strategy is the right play? Not exactly.

Even in those chaotic years, a disciplined approach still performed better than randomly picking multiple upsets. Our data from 2018 shows that a conservative strategy won bracket pools 3.8 times more often than expected.

The public often misses the right upsets. In 2018, for example:

• The average public bracket had 21.6 first-round wins.
• A more disciplined approach averaged 23.9 first-round wins.

Similarly, in 2023, the public averaged 21.7 first-round wins, while a calculated strategy averaged 23.7. Even when chaos unfolded, those who avoided reckless picks gained an edge.

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When Should You Take More Risks?

While playing it safe works in most standard pools, there are exceptions. If you’re in a large pool with hundreds of entries—or if your pool offers bonus points for picking upsets—then a more aggressive approach may be necessary.

For example, some pools award points based on seed difference (e.g., a No. 12 beating a No. 5 earns 8 points instead of 1 point). In these formats, taking more calculated risks can be worthwhile, but it’s still about smart risk allocation rather than blindly chasing upsets.

The Key to a Winning Bracket

The biggest mistake players make in bracket pools is picking too many upsets. A smart strategy means:

• Selecting a few well-researched upsets, not chasing long shots.
• Sticking with favorites where they provide the best value.
• Adapting your risk level based on your pool size and scoring rules.

For smaller pools, playing it safe and letting others make mistakes is often the best move. In larger pools, strategic risk-taking can help separate you from the pack.

March Madness will always be unpredictable—but that doesn’t mean your bracket has to be. The right mix of upsets and safe picks is what separates the winners from the rest.

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