20 most shocking NCAA Tournament upsets that put the ‘madness’ in March

CHARLOTTE, NC - MARCH 16: K.J. Maura #11 and Jairus Lyles #10 of the UMBC Retrievers talk during the first round of the 2018 NCAA Men's Basketball Tournament against the Virginia Cavaliers at the Spectrum Center on March 16, 2018 in Charlotte, North Carolina. The Retrievers won 74-54. Photo by Mitchell Layton/Getty Images) *** Local Caption *** K.J. Macura;Jairus Lyles
CHARLOTTE, NC - MARCH 16: K.J. Maura #11 and Jairus Lyles #10 of the UMBC Retrievers talk during the first round of the 2018 NCAA Men's Basketball Tournament against the Virginia Cavaliers at the Spectrum Center on March 16, 2018 in Charlotte, North Carolina. The Retrievers won 74-54. Photo by Mitchell Layton/Getty Images) *** Local Caption *** K.J. Macura;Jairus Lyles /
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5. No. 15 Richmond over No. 2 Syracuse – 1991

  • Richmond wins 73-69

There is nothing like the first time, and that mantra certainly holds true for our first 15-over-2 upset of all time. That came back in 1991 when Richmond took down Syracuse to set the stage for more future madness out of the 15-2 matchup.

The Orange had become a traditional Big East power under Jim Boeheim, who saw Syracuse go 25-5 during the regular season to earn a two seed. This particular Syracuse roster featured three future NBA players, but they were also set up with a very dangerous 15 seed in Richmond.

The Spiders had developed a reputation as dragon slayers, knocking off Charles Barkley‘s Auburn team as a 12-seed in 1984 and the defending national champion Indiana Hoosiers as a 13-seed in 1988. That edition of the Spiders made it all the way to the Sweet 16 so there was no shot the program would be intimidated by Syracuse.

15-seeds had not done well against 2’s since the field expanded to 64 teams in 1985 but Richmond was in complete control in the second half against Syracuse. The Spiders eventually built a 10-point lead to withstand a late Orange push to pull off the 73-69 upset.

This win was monumental in the landscape of the NCAA Tournament because it was the first time a truly elite regular-season team was knocked off in the first round. All of the 15-seeds that have scored wins since owing some thanks to the Richmond Spiders, who demonstrated that it could be done.