Targeting 5 opening-round upsets to kick off the madness

It's time for everyone's favorite part of preparing for the NCAA Tournament: picking upsets. The lower seeds shocking the world is why the Madness moniker follows March. Without upsets, this tournament wouldn't be so enthralling. They also lead to profitable bets if you fire on the right underdogs.

In this article, we're targeting the bracket-busting upsets that can lead to big money if you nail these moneyline underdogs. And this feature doesn't include upsets like UC San Diego, Creighton, or Arkansas. Although those teams are underdogs, those point spreads are fewer than five points. We'll save those for our best Thursday and Friday bets.

No. 13 High Point +7.5 (+290) over No. 4 Purdue

Purdue has lost six of its last nine games, almost entirely because of its horrific defense. The Boilermakers allow opponents to shoot 56% from 2-point range, the worst mark of any tournament team. Their perimeter defense is also non-existent, which High Point will exploit with shifty guards who can get into the lane.

The Panthers have won 14 consecutive contests, the nation's second-longest winning streak. However, they played only one top-100 opponent all season. They struggle against pick-and-roll heavy guards like Braden Smith, so this will likely be a high-scoring contest. High Point is a respectable shooting team and should score at will against Purdue, which has trended downward over the last month.

No. 11 Drake +6.5 (+220) over No. 6 Missouri

Drake has tested the theory that Division II players can compete at the Division I level. The Bulldogs' squad consists of many former Divison II hoopers who have proven they were ready to compete against elevated competition.

Drake plays a deliberately slow brand of basketball, setting up its offense almost entirely in the halfcourt. The group averages the fewest possessions per game in the country. Fewer possessions usually lead to a lower score and a better chance of an upset.

Mitch Mascari is one of the tournament's best 3-point shooters and plays nearly the entire game (38.5 minutes per game). Missouri's defense can't fall asleep when locating Mascari.

The Bulldogs' formula revolves around slowing the game down, getting to the free-throw line, crashing the offensive glass, and forcing turnovers. They have the third-best opponent turnover rate among tournament teams and the seventh-best offensive rebounding rate. Lower-seeded programs often use that recipe to pull off upsets.

Drake's slow pace helps hold opponents to 58.4 points per game, the best scoring defense of any tournament program. The Bulldogs have the formula to upset Missouri, which lost five of its last seven contests.

No. 12 Liberty +7.5 (+260) over No. 5 Oregon

Liberty is the nation's fifth-best 3-point shooting squad, drilling 39.5% of its threes. A mid-major with as many prolific shooters as the Flames is primed to play spoiler and potentially go on a Cinderella run. They also defend at a high level, allowing 62.9 points per game and holding teams to 28% 3-point shooting, the third-best mark in the tournament.

Oregon is already a below-average shooting team and doesn't have enough offensive weapons to keep up if Liberty gets hot from three. The Flames' weakness is often mediocre rebounding, but the Ducks aren't a strong rebounding group either. Oregon had an impressive season in its first year in the Big Ten, but its run will end in the Round of 64.

No. 13 Yale +7.5 (+270) over No. 4 Texas A&M

Texas A&M is one of the worst 3-point shooting teams in the tournament, yet its offense survives because of its dominant offensive rebounding. The Aggies clean up 40% of their misses, the best offensive rebounding rate in the country. Nearly 23% of their points come from second-chance opportunities, the highest percentage in the tournament field.

That strength is why Yale is a brutal matchup for Texas A&M. The Bulldogs are a physical squad that'll neutralize the Aggies' advantage on the glass. Yale has the tournament's eighth-best opponent offensive rebounding rate. It's also one of the best 3-point shooting teams in the tourney but struggles to defend the three. Still, Texas A&M doesn't have the shooters to take advantage.

Mid-majors rarely pull off upsets two years in a row - No. 13 Yale defeated No. 4 Auburn last year - but the Bulldogs were dealt the perfect opponent in what will be a physical showdown.

No. 14 Lipscomb +14.5 (+900) over No. 3 Iowa State

Iowa State is limping into the Big Dance. Keshon Gilbert is out for the tournament, a major blow to the Cyclones' backcourt. Although they've played without Gilbert a few times this season, he's a key part of their offensive operation as the assist leader. Iowa State had the makings of a national title contender when it was at full strength early this season, but it lost four of its last seven games.

For those wondering, Lipscomb is a small private school in Tennessee. It won 25 contests as a member of the Atlantic Sun.

Iowa State's defense leads to offense, forcing turnovers and scoring in transition. However, Lipscomb rarely turns the ball over. It typically doesn't play the type of athletes on Iowa State, but this is March. The Bisons will play like they have nothing to lose while all the pressure is on the Cyclones. The point spread indicates this is an unlikely upset, but why not be on the right side of history?

Sam Oshtry is a sports betting writer at theScore. You can follow him on X @soshtry for more betting coverage.