March Madness Upset Predictions for the First Round

The Akron Zips possess the shooting ability to send the Wildcats back to Arizona.

Phil Naessens - Betting Analyst at Covers.com
Phil Naessens • Betting Analyst
Mar 21, 2025 • 07:00 ET • 4 min read
Tavari Johnson Akron Zips NCAAB
Photo By - Imagn Images. Tavari Johnson (5) drives to the basket against Miami.

It's the craziest month on earth. The intensity is unlike any other, and the pressure and expectations from being a heavy favorite or a top seed can cause some of these teams to bend and even break.

We have 16 games on today's docket, and I’ve found three underdogs who could become March Madness lore.

Read on as I share my March Madness picks for Thursday, March 21. 

March Madness upset predictions

Baylor moneyline (-105 bet365)

The announcement that Baylor Bears guard Langston Love would attempt to play has essentially made Friday's game a pick-em.

At least we can get a decent price on a Baylor squad with an elite offense and a Top 57 KenPom defense stout enough to upset the Mississippi State Bulldogs.

Friday's combatants are essentially the same. Both have elite offenses and better-than-average defenses and play on a neutral court. However, Baylor has more than just some Love for Mississippi State.

Baylor plays slow-tempo, high-percentage basketball, making 35% of its 24 long-distance attempts. MSU has been crushed by the triple all season long, and if the Bears can make a few early, they could go into cruise control behind their slow pace and elite stop unit.

The Bears are playing well down the stretch and are solid from the charity stripe. Love's return helps, but with or without him, Baylor looks good for pulling off an upset.

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Oklahoma moneyline (+200 at bet365)

The UConn Huskies aren't what they used to be.

They've had incredible defenses in the past, but this one isn't one of them. A KenPom No. 95 defense with a leaky perimeter defense is suitable for most, but not for UConn.

Allowing 35% from downtown could become problematic because the Oklahoma Sooners drain 37% of their 23 attempts from long range, not to mention a robust 55% effective field goal percentage.

Knocking down the three-ball is essential, but so is defending. Oklahoma is No. 70 at KenPom, and it meets an elite but sometimes inconsistent offense with occasional turnover issues.

UConn snipers Solo Ball and Liam McNeely will have their hands full against a Sooner's stop unit, allowing 30.5 % from downtown this season.

It's a tall order; Oklahoma is a 2:1 underdog for a reason.

UConn has all the experience in the world. Still, frosh sensation Jeremiah Fears and the Sooner's offense will make life difficult for the Huskies, and this Oklahoma stop unit can slow UConn enough for a chance to pull off the upset.

Akron moneyline (+750 bet365)

The Akron Zips are heavy underdogs in the East Region matchup against the Arizona Wildcats\.

The Akron backcourt is one of the best in the country. Nate and Tavari Johnson average 27 points between them, and Isaiah Gray shoots 50% from the floor and 39% from beyond the arc.

The Akron trio is part of a Zips group that attempts the sixth-most 3-pointers nationally. They've also drained 36% of their 31 attempts, and their run-and-gun style of play has led to nearly 85 points per game.

Akron is in luck. Arizona is a fast-paced team that doesn't always defend the triple well, and if the Zips get hot from downtown early, things could get dicey for the Wildcats.

The Zips will have to defend Caleb Love and the Wildcats. Love can lay the occasional stinker, and Zona's offense has sometimes been inconsistent.

This bet is a long shot, but stranger things have happened. Akron has won 21 of 22 and can score enough to pull off the upset.

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Phil Naessens
Betting Analyst

Prior to joining Covers in 2022, Phil Naessens spent 38 years as a resident tennis pro in Las Vegas, Mykonos, and Corfu Greece. He’s the past host of the Phil Naessens Show (Armed Forces Radio), and currently hosts the tennis betting podcast, This Week in Tennis.

Phil is the author of the Betting 101 series (MLB, NFL, NCAAF, and Tennis) and has written for numerous publications including SB Nation, FanSided and Lenny Melnick Fantasy Sports. Phil curates the Chip and Charge Tennis Newsletter and pens a weekly tennis column called “10 Things About the ATP Tour," for Passing Shot Productions. 

His favorite sports to bet on are tennis, MLB, WNBA, Euro men’s and women’s hoops, NCAA sports, NFL, and the NBA. Phil has numerous betting accounts in the US and Europe and his best advice is to line shop for the best value possible.

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