March Madness Upset Predictions: Most Likely Cinderella Teams

When it comes to March Madness brackets, everyone knows the deal. 

A correct upset pick is worth its weight in gold. (If you’re betting into the college basketball odds market, it can quite literally be worth some gold.)

I’m hammering out a lot of good NCAA Tournament content right now, including these First Four best bets and lots of ongoing analysis of the college basketball national championship odds.

Here, I’m explaining the rationale I see for some of the biggest potential upsets of the 2025 NCAA Tournament. These potential upsets are valuable to bettors, who are chasing direct financial gain via the odds, but also bracket pool players, who must weigh the potential risk and reward of calling for major upsets early in the tournament. 

March Madness Upset Predictions

UC San Diego vs. Michigan Prediction

Until this year, UC San Diego was one of several teams that were ineligible for the NCAA Tournament because it was transitioning to Division I.

That ineligibility finally elapsed ahead of the 2024-25 season, and the Tritons wasted no time in dominating the Big West and grabbing its first-ever bid to the Div. I NCAA Tournament. 

Here, they face Michigan in the dreaded 12 v. 5 hole, where they should be taken seriously as a potential Cinderella. 

UCSD generates great ball pressure and has a top 60 mark for both adjusted offensive efficiency and adjusted defensive efficiency. As a result, it has the longest active winning streak in college basketball right now: 15 wins in a row.

There’s a reason the Tritons have one of the shortest point spreads of any dog in the first round. They’re live to win. 

At this point, the only thing keeping UCSD from becoming the annual trendy upset pick is the fact that most fans have never heard the name before.

Upset Prediction: UC San Diego +125

North Carolina vs. Ole Miss Prediction

March Madness asks college basketball fans to do something difficult, which is that we must differentiate between what a team deserves and what a team is capable of.

As many have said this week, UNC’s inclusion in the field of 68 was sketchy at best. But no one who’s watched the Tar Heels doubts their ability to score the basketball. (Their lousy defensive prowess is another story.)

Amusingly, UNC draws a perfect foil in San Diego State, which is a gritty defensive team that struggles to generate offense. 

In this modern age of sports, good offense usually wins out. I think North Carolina could prove a successful contrarian pick in the face of an onslaught of doubt and criticism. 

I wrote about why I like the under in this game in my First Four predictions article. However, when it comes to advancing teams in my bracket or handicapping BetMGM’s Sweet 16 odds, I’ll chase the contrarian play with a First Four team that advances out of the Round of 64. Give me UNC over San Diego State, Ole Miss, and Iowa State.

Upset Prediction: North Carolina

New Mexico vs. Marquette Prediction

Marquette has struggled in the NCAA Tournament in recent years, and they haven’t exactly closed out the 2024-25 pre-tournament season with a strong record down the stretch. 

Enter New Mexico, which won a very competitive Mountain West regular season this year and looks the part of a strong, defense-oriented tournament team. 

No. 10 seeds have won 40% of their first-round games against No. 7 seeds since 2018, which means handicappers and bracketologists alike should be hunting for proper spots to eliminate No. 7 seeds early. This seems like a likely spot, which is reflected in the relatively short moneyline price for New Mexico. 

Upset Prediction: New Mexico +145

High Point vs. Purdue Prediction

Purdue may have played all the way to the Final Four last year, but the broader historical record has not been kind to Matt Painter’s career NCAA Tournament record. The Boilermakers have a long history of disappointing exits in March.

It feels like the public may have forgotten all about that after last year’s revenge run. That’s a big opportunity for both bettors and bracketologists since Zach Edey ain’t walking back through the door to suit up for Purdue.

High Point plays a fast pace that scores points and could frustrate a more methodical Big Ten offense like Purdue. This is one where more conservative bettors might opt for the 8.5 points, and I wouldn’t blame them. 

That said, multi-round elimination events like the NCAA Tournament are the exact time to be more aggressive with longshot underdogs. If you’re not, then you’re leaving a lot of potential return on the table. I’ll chase the big plus money with High Point. Given the historical likelihood that Purdue flames out sooner rather than later, I’m pretty comfortable advancing the Panthers in my brackets, too.

Upset Prediction: High Point +300

Akron vs. Arizona Prediction

Akron is another team that enters the NCAA Tournament with a long, lofty winning streak. 

The Zips have locked up a pretty good mid-major conference in the MAC, winning their way back to the NCAA Tournament for their third bid in four years. They also earned a spot in the Big Dance in 2024 and 2022.

Akron hasn’t broken through with a first-round win yet, but the MAC has fielded competitive NCAA teams in recent years. That includes first-round wins in 2021, 2019, and 2018. 

The 2018 win is particularly interesting because it was No. 13 seed Buffalo that scored a win against No. 4 seed Arizona. 

Can Akron finally break through and score another MAC win against the Wildcats? The market seems awfully skeptical at +700, perhaps because Arizona just played in the Big 12 title game against Houston. 

Traditionally, though, conference tournament runs can be way overread as a projection tool for NCAA Tournament success. I would argue that Akron is quite underpriced at +725, making them a questionable choice for bracketology concerns but an excellent candidate for moneyline bettors.  

Upset Prediction: Akron +725

Lipscomb vs. Iowa State Prediction

Lipscomb is building a nice program in the Atlantic Sun, but they’re probably not quite at the full-on Cinderella stage just yet. In a stronger year, this team would probably be a No. 15 seed. That explains the long odds for an outright win.

Still, Lipscomb presents an interesting opportunity to be against Iowa State’s backcourt, which has been struggling with injuries for weeks leading up to the NCAA Tournament. 

This is another case where I fully understand bettors who want the +14.5 rather than the big return with the moneyline. 

For bracketologists, though, Lipscomb is a great upset to consider in the first round – Iowa State is probably doomed because of bad health anyway, so the long-term risk of picking against them is pretty minimal. The Cyclones NCAA Tournament history backs up a fade, too – they pretty much never advance beyond the Sweet 16. 

Upset Prediction: Lipscomb +775