March Madness First Round Upset Predictions: 2025 NCAA Tournament Day One Underdog Picks

Mar 8, 2024; Dayton, Ohio, USA; Dayton Flyers guard Enoch Cheeks (6) shoots the ball against Virginia Commonwealth Rams guard Joe Bamisile (22) and forward Kuany Kuany (13) during the second half of the game at University of Dayton Arena.
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Caleb Wilfinger

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Deputy Editor for Pickswise with years of experience handicapping and giving out winning picks. Lover of all US sports and Southampton FC. For Caleb Wilfinger media enquiries, please email contact@pickswise.com.
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At long last, the first round of the NCAA Tournament is here, and we have 16 great games on the schedule for Thursday’s loaded March Madness slate. Who knows what the day’s events will bring, but it’s likely that we’ll see a few upsets, which is part of what defines these early rounds of the NCAA Tournament each season. You can be almost sure that at least 1 team will deliver a program-defining win each year, no matter if that team ultimately falls short of a Final Four or even an Elite Eight appearance.

There will always be surprises; the key to building better brackets and better betting is to identify the right ones. Last year, we saw NC State, Grand Canyon, Yale and Oakland all pull off significant upsets in the opening round. What will this year’s installment bring? It’s almost time to find out. Let’s get into my best March Madness underdog picks for the opening day of the NCAA Tournament, while you can also check out our March Madness predictions for EVERY game!

March Madness underdog pick: VCU Rams ML over BYU Cougars (+130)

The one thing that worries me about VCU in this game is the fact that the Rams just played a very physical game against in-state rival George Mason last Sunday to win the Atlantic 10 conference tournament. Now, the Rams will have to play a slightly more rested BYU team in a setting that the Cougars should be a bit more comfortable in. With that said, I still like VCU to pull off the small upset in a game that features an extreme contrast in styles of play between these two teams.

BYU is largely a jump-shooting based team that has the ability to knock down shots from all over the court, thanks to the myriad of quality shooters they can have on the floor at any given moment. Conversely, VCU is a team that prides itself on shutting down its opponents, as the Rams are the top defense in the nation in effective field goal percentage, while also sitting at 4th nationally in two-point percentage defense.

The Rams are also known for their high-pressure defense, which should see consistent success against a BYU team that is no stranger to turning the ball over. BYU is outside the top 200 in turnover percentage on the season, and the Cougars just committed well over 20 turnovers in a recent game against Iowa State. With that in mind, it’s hard not to back a VCU defense that also defends the three-ball very well, which is obviously where this BYU team wants to live. The Rams are also rock solid on the glass (11th in offensive rebounding rate), so they just hold too many advantages for me to overlook them in this matchup and look a strong March Madness underdog pick.

Get ready for the madness with our expert’s NCAA Tournament winner predictions, including a +6000 longshot! Plus, don’t miss our comprehensive March Madness 68-team bracket guide, featuring analysis of EVERY team in the tournament!

March Madness underdog prediction: UC San Diego Tritons ML over Michigan Wolverines (+125)

Just a few years removed from jumping up to the Division I level, UC San Diego has been one of the best stories in college basketball this season, winning 30 games en route to a Big West title and a shot at knocking off the Big Ten champion Michigan Wolverines. It just so happens that the Tritons are well-equipped to pull off the upset as short underdogs in this game.

From a situational spot perspective, this Michigan team is coming off playing 3 hard-fought games in as many days en route to winning the Big Ten tournament title last Sunday. Now, the Wolverines have to travel to Denver to play at altitude against a UC San Diego team that is a very well-rounded group, and the numbers back it up. In fact, the Tritons are one of the highest-rated mid-major sides ever by the predictive analytic sites, such as KenPom, Barttorvik, etc.

Part of why UC San Diego will be live in this game is that this is a pretty difficult team to prepare for, especially on a short turnaround. The Tritons play a unique style of basketball that emphasizes unselfishness and turning down good shots for great shots, which is part of why they have a very consistent offense (58th in adjusted efficiency, 30th in two-point percentage, 30th in effective field-goal percentage).

However, the biggest edge in this game for Eric Olen’s team is their ability to force a ton of turnovers (2nd nationally in turnovers forced), while also not turning the ball over themselves. This strength should especially come in handy against an extremely turnover-prone Wolverines offense (328th in turnover percentage) that could find themselves in big trouble on Thursday against an excellent UC San Diego unit that is elite at defending the paint (93rd percentile in rim defense efficiency). Michigan is also due for some massive close-game regression after winning a ton of matchups by 2 possessions or fewer throughout Big Ten play. All things considered, I’ll take the Tritons to pull off the outright upset as my next March Madness underdog prediction in a game that should come down to the wire.

Let the madness begin! Shoot for the moon with our 16-leg March Madness millionaire parlay at ENORMOUS +33679 odds!

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