How to Pick Upsets in 2025 March Madness Brackets and a Look at Past History

Updated: Mar 8, 2025, 3:57 PM ET | First published: Mar 8, 2025, 12:58 PM ET

Written by Dave Garofolo, Content Producer

Picking the right upsets in your March Madness bracket is critical to success so we're analyzing past results to identify how to approach your 2025 NCAAB Tournament picks.

2025 March Madness Bracket, NCAAB Tournament Predictions, Upset picks — How many upset is the right amount to pick in a March Madness bracket? Let's find out.

For nearly four decades, March Madness has delivered some of the most thrilling upsets in sports. With the NCAA Tournament field expanding to 64 teams in 1985, underdogs have consistently defied the odds and turned even the most analytical college basketball predictions on their head, creating some of the most memorable moments in college basketball history.

They can also make or break a March Madness bracket and understanding the frequency and distribution of these upsets can help you craft a smarter bracket strategy.

Beyond our Best CBB Bets, college basketball props, and NCAAB Tournament Futures, Dimers will release a variety of team and upset brackets once the tournament field is finalized on Selection Sunday to help you find the right upsets for your bracket, but until then, we can analyze past results and garner some data. Be sure to check out our NCAAB Tournament Futures Betting Strategy for how to find value on a champion, as well.

What is an Upset?

Before diving into the numbers, we need to clarify what constitutes an upset.

Realistically, it means a lower seed beating a higher seed, but close-seeded matchups like an 8-seed vs. 9-seed matchup in the first round, or 1-seed vs. 2-seed late in the tournament don't quite fit the bill as those teams are expected to be more closely matched.

Instead, we’re focusing on genuine shockers—when lower-seeded teams overcome significant ranking gaps, so for the purpose of this analysis, we'll consider an upset a situation where a team seeded 5 or more spots lower beats their opponent. This removes the 8/9 and 7/10 matchups from the first round.

How Often Do Upsets Happen?

Looking back at the last 39 tournaments (since the 1985 expansion), at least 10 upsets have occurred in 15 of those seasons, with an average of 8.5 upsets per tournament.

The highest number of upsets on record happened twice, with 14 upsets in consecutive years in the 2021 and 2022 tournaments, while the lowest came in 2007 with just three.

In recent years, upsets have become more frequent, including some of the biggest ever—there have been at least 10 in nine of the last 13 tournaments. Most recently, the 2023 tournament saw 10 upsets, while the 2024 edition had nine.

March Madness, NCAAB Tournament, Upset picks — *The 2018 UMBC Retreivers became the first-ever 16-seed to beat a No. 1 seed.*

How Many Upsets Should You Pick?

If you're aiming for an optimal bracket balance, targeting around 11 upsets can be a strategic choice, as that number has hit five times (1986, 2002, 2006, 2011, and 2013) and is above the average of 8.5 and sweet spot of 10.

On the safer side, selecting between five and eight upsets keeps you within the range of past tournament trends without taking too many risks. Only once since 2010 have we seen fewer than seven March Madness upsets, while the aforementioned 2007 tournament with three upsets remains the lone instance where fewer than five occurred.

Where Do Upsets Happen Most?

The first round is where upsets are most frequent, given the sheer number of games and variability in team matchups. Historically, about half of all tournament upsets occur in this round.

As teams advance, the probability of lower-seeded teams continuing their Cinderella runs decreases as the opposition talent increases, but some major upsets still occur in later rounds.

First Round Upset Frequency:

Seed Matchup	Lower Seed Wins	Higher Seed Wins	Upset Percentage
16 vs. 1	2	154	1.30%
15 vs. 2	11	145	7.10%
14 vs. 3	23	133	14.70%
13 vs. 4	33	123	21.20%
12 vs. 5	55	101	35.30%
11 vs. 6	61	95	39.10%

To refine your bracket selections, it's helpful to analyze first-round matchups with a history of upsets. Additionally, keeping an eye on potential second-round shockers can add an edge to your picks, as 46 individual 2-seeds have lost to a No. 7 or No. 10 in the second round since 1985.

Biggest Upsets in March Madness History

Below is a list of the biggest upsets since the 1985 expansion of the NCAAB Tournament, beginning with the lowest seeds. For this list, we're looking at the 15 and 16 seed upsets. We'd go with all teams with a seed gap of at least 10 or more, but there have been 23 instances where a 14-seed beat a 3-seed.

2018 - #16 UMBC beats #1 Virginia, 74-54
2023 - #16 Fairleigh Dickinson beats #1 Purdue, 63-58
1991 - #15 Richmond beats #2 Syracuse, 73-69
1993 - #15 Santa Clara beats #2 Arizona, 64-61
1997 - #15 Coppin State beats #2 South Carolina, 78-65
2001 - #15 Hampton beats #2 Iowa State, 58-57
2012 - #15 Norfolk State beats #2 Missouri, 86-84
2013 - #15 Florida Gulf Coast beats #2 Georgetown, 78-68
2016 - #15 Middle Tennessee beats #2 Michigan State, 90-81
2021 - #15 Oral Roberts beats #2 Ohio State, 75-72 (OT)
2022 - #15 Saint Peter’s beats #2 Kentucky, 85-79 (OT)
2023 - #15 Princeton beats #2 Arizona, 59-55

Final Thoughts

Selecting the right number of upsets is a balancing act, so by using these guidelines, you should be able to get the right amount in your bracket, though picking them correctly is a whole other game entirely, which is where you'll want to utilize Dimers Pro features for the tournament.

Upset Guidelines:

15 upsets is too many, but 5 is likely too few
You should aim or 8-11 upsets in your bracket
Expect at least one 2-seed to lose in the second round
Include at least one 1-seed to lose in Rounds 2 & 3

While picking 15 upsets is likely too aggressive, selecting only five may leave points on the table. Based on historical trends, a well-calibrated bracket should include roughly eight to 11 upsets, with a strong focus on first-round surprises and By striking the right balance, you can maximize your chances of crafting a winning bracket while still embracing the unpredictability that makes March Madness so special.

Dimers' College Basketball Betting Resources for the 2024-25 Season

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Best CBB Props: Player edges and projections from our predictive analytics model
CBB Futures Odds: Who will win the 2025 March Madness Tournament?
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To make sure you get accurate and helpful information, this guide has been edited by Nick Slade as part of our fact-checking process.

Written by

Dave Garofolo

Content Producer

Dave Garofolo uses sophisticated AI-driven analytics to make predictions and evaluate player performances in the NBA, MLB, NFL, NHL, NCAAM, and PGA TOUR tournaments, crafting insightful game and prop previews.

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