Betting on Cinderella: Top 5 first-round upsets since the field expanded

While our annual pursuit of the perfect bracket begins anew this week, we recognize it is more likely that we will be struck by lightning than go 64-0 the next three weeks (68-0 if you want to make it all the more impossible by including the First Four games).

Why has the undefeated bracket been so elusive? The 1st Round is usually the primary offender.

The Madness really became a thing in 1991 when Dick Tarrant’s Richmond Spiders as a 15-seed upset Billy Owens and the 2nd-seeded Orange of Syracuse. No way anyone not holding a diploma from the University of Richmond had the guts to call for that result. There had been upsets prior to that tilt but that was the biggest from a seeding perspective. The Madness had reached new heights.

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It would take days to lay out all the upsets since the Spiders’ win 33 years ago, so let’s stick to the Top 5 Round 1 upsets of the last six years. We list them in inverse order on the shock meter.

#5 Arizona vs. Princeton (2023)

Not the biggest upset in last year’s opening round (spoiler alert), but the Wildcats were stunned by Princeton. The 15-seed Princeton reeled off the final nine points of the game to win 59-55 over the No. 2 seed Arizona.

#4 Kentucky vs. Saint Peter’s (2022)

An 18.5-point underdog, the No. 15 seed Saint Peter’s Peacocks pulled off the shocker with an 85-79 overtime win over John Calipari and the No. 2 seed Kentucky Wildcats.

#3 Ohio State vs. Oral Roberts (2021)

Another 15 defeats a 2 and again it happens in overtime as the Golden Eagles took down E.J. Liddell and the Buckeyes 75-72.

#2 Purdue vs. Fairleigh Dickinson (2023)

A seismic shocker which would have been greater if not for the fact that the #1 upset of all-time happened just five years earlier.

#1 Virginia vs. UMBC (2018)

The first time in history that a 16-seed took out a 1-seed as UMBC humbled UVA 74-54.

Not sure that Cavaliers’ loss was a bigger upset Purdue’s, but it was the first time a 16 took out a 1 and so it reigns all-time atop the list of first round upsets.

Saint Peter’s is back as a 15-seed this season. Do the Peacocks have another upset in them? They are 21.5-point underdogs to Tennessee. How about Tournament first-timer Stetson? The deck is so stacked against them the sportsbooks are not even offering a line for that game.

The bigger questions are do you have the guts to pencil one in on your bracket or bet one with your favorite sports book?

Enjoy the Madness.