March Madness Upset Predictions for the First Round

Phil Naessens breaks down the first round of March Madness and offers his best March Madness upset predictions for Thursday, March 20.

Phil Naessens - Betting Analyst at Covers.com
Phil Naessens • Betting Analyst
Mar 20, 2025 • 09:00 ET • 4 min read
Drake Bulldogs guard Bennett Stirtz (14) reacts during the second half of the Missouri Valley Conference Tournament Championship.
Photo By - Imagn Images. Drake Bulldogs guard Bennett Stirtz (14) reacts during the second half of the Missouri Valley Conference Tournament Championship.

The road to the Final Four is typically filled with stumbling blocks the higher seeds must navigate.

Thursday’s March Madness 16-game slate has some potential stumbling blocks, and I’ve narrowed it down to my three favorite March Madness upsets that could help us make some money. 

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

March Madness upset predictions

Drake Bulldogs moneyline (+230 bet365)

No. 11 seed Drake Bulldogs won the Missouri Valley Conference with arguably the best defense amongst the Mid-Majors. 

Drake is better than 2:1 underdogs, but I like their chances of upsetting the No. 6 Missouri Tigers.

Drake surrenders the fewest points (58) in D1 play behind a tenacious defense, allowing 44% shooting from the field and a stingy 31% from downtown.

Drake may give up some size on the boards, but this Bulldogs group are good team rebounders-they boast a +5.6 rebounding margin, but slowing KenPom's No. 5 ranked O-Unit will be a tall order because Missouri can score with anyone.

Missouri's game totals routinely end in the 180s or better. They play fast and are elite shooters from everywhere except the charity stripe. 

Drake could pull off an upset, but only if the stop unit can keep Missouri in the 70s.

Missouri's fatal flaw is its defense—it doesn't defend well. Drake isn't a high-scoring group, but it is consistent, and if the Bulldogs' defense comes through, Drake can beat Missouri. 

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Arkansas Razorbacks moneyline (+180 at bet365)

Had you told me in November that John Calipari and the Arkansas Razorbacks would meet Bill Self and the Kansas Jayhawks in the opening round of the NCAA Tourney, I may have laughed.

The Jayhawks are loaded with talent. However, they enter the Big Dance not playing their best basketball — they've dropped three of five and have only played .500 ball during their last ten games.

Kansas defends well, but its offense is inconsistent. They shoot too fast into the clock, and they'll have their hands full with Boogie Fland and the Razorbacks.

Arkansas has won three of four. Fland's return to the lineup will boost the Razorbacks. He's a tremendous playmaker, and if the frosh guard from NYC is fit, Arkansas can make some noise.

This game should be closer than the number. Both are sub .500 ATS with below .500 road records.

Both defenses are elite. The winner will be the one that executes best. I like the Razorbacks' chances against the awkward-looking Jayhawks.

VCU Rams moneyline (+125 at bet365)

The BYU Cougars have dropped two straight NCAA openers as the No. 6 seed vs. the 11 seed, and the third time might not be the charm.

That's because the VCU Rams aren't your ordinary 11 seed. They boast a Top 45 offense and Top 25 KenPom defense, and I like to back that type of underdog.

Especially when that underdog wins on the road (7-3) and covers the spread everywhere (20-11-2 ATS).

The Rams accomplished this with a defense that chases shooters off the arc at an elite rate with the top effective field goal percentage allowed at KenPom.

They turn 14 turnovers into nearly 17 points per game and face a BYU offense that is sometimes sloppy enough with the ball to cause them trouble against the Rams.

BYU will be the best offense the Rams' elite defense has faced this season. The Cougars have won nine of ten games, but their three-point defense is shaky.

VCU drains nearly 10 threes per game, and if they get hot, BYU could experience deja vu all over again. 

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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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