March Madness Upsets: The Teams We’re Betting On

March Madness Upsets: The Teams We're Betting On

The NCAA men’s basketball tournament is the epitome of the sports world’s “anything can happen” mantra. The most shocking March Madness upsets are hard to spot ahead of time, but a few matchups in the 2021 bracket stand out as strong value opportunities for anyone participating in a pool, betting on individual games, or just filling out their 68-team bracket for fun.



The 2021 tournament will probably not include an upset as shocking as No. 16 seed University of Maryland, Baltimore County’s historic win over No. 1 seed Virginia in 2018. This year, none of the No. 1 seeds are vulnerable enough to get beaten in the first round of the tournament. But March Madness has taught us to keep our eyes peeled for the occasional shocker, and the general weirdness of this year could encourage upsets, too.

The tournament’s opening-round matchups are March 19 and 20, and games run through the national championship on April 5. Here are five games in the round of 64 where the underdogs could pull off major March Madness upsets.

No. 10 Maryland

No. 10 Maryland over No. 7 UConn, East Region

The Terps have no offensive rebounding presence, and they tend to run into trouble when they play teams that can assert themselves inside. (Maryland only has one rotation player taller than 6’8’’, and that player, Galin Smith, is only in the rotation because of talent scarcity.) The Huskies, on the other hand, are a good offensive rebounding team.

But Maryland boxes out reasonably well on defense, and the Huskies are not a great shooting team from the field. Maryland has also been tested by a brutal Big Ten schedule. It wouldn’t be surprising if the Terps got into the round of 32 as a double-digit seed.

winthrop men's basketball
No. 12 Winthrop Courtesy Image

No. 12 Winthrop over No. 5 Villanova, South Region

Winthrop likes to push the pace. The Eagles take just 15 seconds (out of a 30-second shot clock) per possession, making them the eighth-fastest-paced team in Division I. They also crash the offensive glass (their 35.7 percent offensive rebounding rate is 12th in D1), and they’re a decent shooting team.

That chaotic playing style could cause some problems for a Villanova team that plays much more deliberately, with an eye toward bleeding the shot clock and not turning the ball over. If the Wildcats get off to a slow shooting start, Winthrop could pounce.

No. 14 Eastern Washington
No. 14 Eastern Washington Courtesy Image

No. 14 Eastern Washington over No. 3 Kansas, West Region

This one is a long shot, but what’s the fun of picking a bracket if you won’t try something between a 14th and 16th seed? The Eagles are another pace-pushing squad that likes to score in transition and use little more than half the shot clock. They make three-pointers (35.9 percent) and foul shots (79.9 percent) at well above average rates.

The Jayhawks just withdrew from the Big 12 Tournament due to a positive COVID-19 test. Even when healthy, they are not a great shooting team, and it seems possible they could go cold long enough for lightning-fast Eastern to build up a lead. The Eagles are at a major talent disadvantage in this game, but they might do things well enough—and fast enough—to be a lot to handle for a struggling version of KU.

No. 13 Liberty
No. 13 Liberty Courtesy Image

No. 13 Liberty over No. 4 Oklahoma State, Midwest Region

Oklahoma State can beat anyone. The Cowboys proved as much by overcoming Baylor in the Big 12 Tournament. But they can also lose to anybody: For example, getting swept by a lousy TCU team that went 1214.

OSU plays fast but could fall behind quickly if shots aren’t falling early against the Flames, who prefer to move the ball around in half-court sets and then make shots. Liberty is one of the best shooting teams in the field and a strong upset candidate. Either way, the clash of styles should make this an interesting game.

No. 12 Georgetown
No. 12 Georgetown Courtesy Image

No. 12 Georgetown over No. 5 Colorado, East Region

Patrick Ewing has the Hoyas playing with a swagger they’ve rarely shown since he played there himself in the early 1980s. Georgetown looked energized in a run to the Big Ten Tournament title, and a lot of March Madness success comes down to finding the hot hand at the right time. (For a recent example, see the 2018 Michigan team that struggled all year before getting hot in February, winning the Big Ten Tournament in March, and going all the way to the national title game.)

Georgetown’s biggest shortcomings are poor finishing around the basket and too many turnovers on offense. But Colorado doesn’t have dominant big men operating inside, and it doesn’t play a high-pressure defense that would force Georgetown to make a ton of turnovers. It wouldn’t be surprising if Ewing’s team mounted a nice little run this spring.

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