Upset Brackets (2025): Our Algorithm’s Top Underdogs

Our model pinpoints the smartest underdogs, crafting brackets set at varying risk thresholds that identify upset potential without sacrificing solid foundations.

In March Madness pools that reward correct upset picks with extra points, Dimers’ Upset Brackets are your best bet.

• Multiple risk levels—choose how bold you want to go
• Data-driven underdog picks based on thousands of simulations
• Perfect for pools that reward bold choices

Choose Your Upset Bracket Risk Level

Dimers has designed six bracket variations, each catering to a different risk tolerance. Whether you prefer a safer approach or want to embrace maximum chaos, we’ve got a bracket for you.

Find the brackets you're interested in below and click "Download now" to get started. If you don't already have a Dimers account, you will be sent to a sign-up page to create an account, then get access to the PDFs. It's free.

• Dimers’ Most Conservative Upset Bracket (#1) – Our safest upset bracket, featuring calculated risk but mostly high percentage. Download now
• Dimers’ Low-Risk Upset Bracket (#2) – A balance of strong favorites and carefully selected upsets. Download now
• Dimers’ Mid-Risk Upset Bracket (#3) – A well-rounded mix of underdogs and favorites. Download now
• Dimers’ High-Risk Upset Bracket (#4) – More aggressive with high-upside underdog picks. Download now
• Dimers’ Wild Card Upset Bracket (#5) – Heavy on Cinderella picks and deep runs for underdogs. Download now
• Dimers’ Chaos Theory Bracket (#6) – Maximum upset potential—bracket insanity at its finest! Download now

Our upset brackets are ranked by risk tolerance. The riskier the bracket, the. 

While the standard March Madness bracket pool simply awards a player point(s) for successfully picking the winner of each of the 63 games in the tournament (excluding the First Four), there are alternative variations that more heavily reward upset picks. 

Dimers has created the brackets on this page to service players participating in these pools by developing data models of varying risk levels to account for these unique competitions. Below are the two most popular examples of alternate bracket pools best suited for our predictions:

• Classic Upset Pool: Players receive a traditional score for correctly picking a winner, plus an upset bonus based on the seed difference. For example, picking a 12 seed to beat a 5 seed might earn a player 8 points. 
• Upset Assassin Pool: Players receive points for winning matchups, and also steal points from the team they defeated. This format especially incentivizes late-round upset picks, as the favorites in those matchups have accumulated more points throughout the earlier rounds of the tournament.

March Madness is notorious for its unexpected outcomes and dramatic upsets—there’s a reason we don’t call it March Mundanity. At Dimers, we understand not only the emotional appeal of rooting for the little guy, but the historical basis for occasionally selecting the underdog. 

Below are three of the most famous examples of upsets from the last 40+ years of the NCAA Men’s Division I Basketball Tournament:

• UMBC vs. Virginia (2018): UMBC (16) made history by becoming the first 16-seed to defeat a 1-seed (Virginia) in the men’s tournament.
• NC State vs. Houston (1983): NC State (6) stunned Houston (1), a team with future NBA stars, to win the national championship.
• Villanova vs. Georgetown (1985): 8-seed Villanova defeated top-seed Georgetown in one of the most surprising championship game results.

In other words...we’re telling you there’s a chance. 

At Dimers, we’re dedicated to delivering reliable sports predictions powered by cutting-edge tech and data-driven insights. Our team of data scientists and machine learning pros has built proprietary models that tap into the latest advancements in AI, machine learning, and simulation techniques to break down every game with precision.

We start with collecting massive amounts of data—from historical stats to live, in-game updates at both the team and player level. Some of this data comes from external sources, while other key metrics we track ourselves. We then apply advanced statistical analysis to uncover patterns, pinpoint critical variables, and refine our predictive models.

Our models process thousands of data points and weigh every possible factor—team and player performance, weather, starting lineups, home vs. away trends, projected minutes, and more. The result? Data-backed insights that help you make sharper picks with confidence.

Best of all, while our advanced data is typically reserved for paying Dimers Pro subscribers, who can use it to get an edge against sports betting odds all year long, the free and downloadable college basketball brackets on this page are the exception.