March Madness: 20 Biggest First-Round Upsets

Perhaps the most interesting and exciting games of the tournament are played in the first weekend.

The format has changed a little this year, but the match-ups on Thursday through Saturday should be just as compelling.

While a 16-seed has never won an opening round game (and maybe never will), four 15-seeds have, instilling in those underdogs the belief that it can be done.

Heavyweights like Kansas, Arizona and Indiana appear more than once on the list of big names that have fallen on the first day.

This is bound to happen because they are almost always a high seed, and sometimes, the gap between being third best in your power conference and being the best in your mid- or low-major conference doesn't seem to be that great.

This season, perhaps more than any other, true upsets might be rare. The parity that this college basketball season has seen has been like no other, and while there are probably two handfuls of teams that could win the whole thing, it would hardly be surprising to see virtually anyone beat anyone else.

And now, 20 of the biggest upsets in the history of the opening round.

20. Canisius 79, N.C. State 78 (1956)

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21 Dec 1996: Coach John Beilein of the Canisius Griffs watches his players during a game against the North Carolina at Charlotte 49ers at the Marine Midland Arena in Buffalo, New York. North Carolina at Charlotte won the game 54-51. Mandatory Credit: Ri

This one probably deserves a place higher up but pre-dates the actual Final Four format.

Second-ranked in the country, N.C. State was a prohibitive favourite to handle Canisius. After squaring off for 60 minutes, Canisius pulled out the one-point win.

It was the longest NCAA tournament game ever to that point and has been matched once but never exceeded.

19. 14-Seed Siena 80, 3-Seed Stanford 78 (1989)

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Mark Brown’s two free throws with three seconds left were the difference as Siena upset the Cardinal.

The story behind the upset is classic. Siena has no nickname, as they had dropped “Indians” prior to the season, so that was unusual.

The ECAC championship game between Siena and Boston University was broadcast on ESPN and witnessed by...no one.

Apparently, a measles outbreak on campus resulted in a quarantine, and other than team members and a few media, no one attended.

Siena won that game in the last second as well.

18. 14-Seed Northern Iowa 74, 3-Seed Missouri 71 (1990)

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The Panthers led by 12 with five minutes to play, but Missouri came back to tie on a three-point play by Nathan Buntin.

With less than five seconds left, Maurice Newby launched a 25-foot three-pointer that rattled in.

Missouri, which had spent much of the year in the Top 10, was done.

17. 13-Seed Richmond 72, 4-Seed Indiana 69 (1988)

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Defending champion Indiana was knocked out early, the first defending champion since Louisville in 1980 to lose their first tournament game the following year.

Rodney Rice scored with less than a minute left to give the Spiders the lead for good.

Some, including Hoosier coach Bobby Knight, didn’t consider this to be a great upset because Richmond had a very good team. 

Still, one would expect the defending champs to be moving on past the first round.

16. 13-Seed Southern 93, 4-Seed Georgia Tech 78 (1993)

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Southern wasn’t even a tourney team.

The conference final of their league, against Jackson State and their star player, Lindsay Hunter, was still going on when the selections were announced.

Apparently, the committee left a 13-seed spot open...for Jackson State. When Southern ended up winning that game, that was the spot they were given.

Unfortunately for Georgia Tech.

15. 13-Seed Indiana State 70, 4-Seed Oklahoma 68 in OT (2001)

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Kelyn Block, minus three teeth, scored five of his 17 points in overtime as the Sycamores beat Oklahoma 70-68.

Sooner star Hollis Price had his triceps torn in the collision with Block, who left the game but returned for the overtime period.

The Sycamores won the Missouri Valley tournament this season for the first time since then.

14. 13-Seed East Tennessee State 87, 4-Seed Arizona 80 (1992)

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ETSU held an 11-point lead at halftime and were in control most of the game in upsetting the Wildcats.

Rodney English led the Buccaneers with 21 points, who lost in the second round to eventual finalist Michigan and the Fab Five.

13. 13-Seed Valparaiso 70, 4-Seed Mississippi 69 (1998)

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Hard to forget Bryce Drew's shot and subsequent reaction as Valpo stunned Ole Miss in the first round.

The Rebels were not exactly tournament mainstays, so this was not as big an upset as the seedings may suggest. However, it was one of the best endings ever.

Forgotten, perhaps, is the fact that it was a great back-and-forth game with three ties and nine lead changes in the second half.

Mississippi's Ansu Sesay missed two free throws with four seconds left. One make would have at least forced overtime.

12. 13-Seed Princeton 43, 4-Seed UCLA 41 (1996)

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14 Mar 1996: Coach Pete Carril of the Princeton Tigers looks on during a game against the UCLA Bruins at the RCA Dome in Indianapolis, Indiana. Princeton won the game, 43-41.

Pete Carril announced his retirement after Princeton had won the Ivy League title the previous week and finally got his NCAA win after several close calls.

Gabe Lewullis scored with 3.9 seconds left, taking a pass from Steve Goodrich and completing one of the Tigers famed backdoor layups to knock off the defending national champions.

It was the lowest winning point total since the inception of the shot clock.

11. 14-Seed Austin Peay 68, 3-Seed Illinois 67 (1987)

Andy Lyons/Getty Images

NORTH LITTLE ROCK, AR - MARCH 21: Head coach Dave Loos of the Austin Peay Governors reacts in the first half against the Texas Longhorns during the first round of the South Regional as part of the 2008 NCAA Men's Basketball Tournament at Alltel Arena on

Tony Raye hit two free throws with two seconds left to give the win to the Governors.

Darryl Bedford, a 6ʼ8” post player, hit five three-pointers, rare because post players rarely shot from beyond the arc, especially as this was the first year of the three-point line.

A 30-foot buzzer-beater in their own conference tournament secured the spot in the NCAA tourney for Austin Peay despite mediocre conference (8-6) and overall (16-11) records.

10. 14-Seed Bucknell 64, 3-Seed Kansas 63 (2005)

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OKLAHOMA CITY - MARCH 18: Donald Young #4 of the Bucknell Bison screams as his team upset the Kansas Jayhawks during the first round of the NCAA Men's Basketball Championship on March 18, 2005 at the Ford Center in Oklahoma City, Oklahoma. Bucknell knock

The first of two consecutive first-round losses for Bill Self and the Jayhawks came when Wayne Simien missed a 15-footer at the buzzer.

Kevin Bettencourt scored 19 points and Chris McNaughton had 14, including the go-ahead
basket with 10 seconds left.

It was the first time in six years that a 14-seed had won in the opening round and the
first NCAA tournament victory in 110 years for the Bison.

9. 13-Seed Bradley 77, 4-Seed Kansas 73 (2006)

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AUBURN HILLS, MI - MARCH 17: J.J. Tauai #10 of the Bradley Braves shoots over the defense of Sasha Kaun #24 of the Kansas Jayhawks during the First Round of the 2006 NCAA Men's Basketball Tournament at The Palace of Auburn Hills on March 17, 2006 in Aubu

At the same venue that had seen No. 3 Iowa go down earlier, Patrick O'Bryant and Marcellus Sommerville led the Braves to a huge upset over Kansas, who featured the likes of Mario Chalmers, Brandon Rush, Julian Wright and Russell Robinson.

The Jayhawks had cut a 14-point lead to three with just under four minutes to go, but that was as close as they would get.

Bradley was one of four Missouri Valley teams in the tournament this season and one of two (Wichita State was the other) that made it to the Sweet 16 that season.

8. 14-Seed Arkansas-Little Rock 90, 3-Seed Notre Dame 83 (1986)

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1989-1990: Notre Dame Fighting Irish coach Digger Phelps confers with a player during a game. Mandatory Credit: Stephen Dunn /Allsport

10th-ranked Notre Dame went into their first-round game at the Minneapolis Metrodome as 17-point favorites over the Arkansas-Little Rock Trojans.

The 14th-seeded Trojans were 15-of-19 from the field and 9-of-11 from the free throw line in the second half to overpower the Irish.

Future pro Pete Myers had 29 points and Michael Clarke scored 27 to lead the Trojans.

7. 14-Seed Weber State 76, 3-Seed North Carolina 74 (1999)

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DETROIT - APRIL 06: The North Carolina Tar Heels mascot celebrates after the Tar Heels defeated the Michigan State Spartans 89-72 during the 2009 NCAA Division I Men's Basketball National Championship game at Ford Field on April 6, 2009 in Detroit, Michi

Who remembers Harold “The Show” Arceneaux?

He and his 36 points staked Weber State to a big lead that just held up as the Tar Heels stormed back in the second half.

Arceneaux scored 32 the next game, an overtime loss to Florida, which nullified a possible Weber State/Gonzaga showdown in the Sweet Sixteen.

6. 14-Seed Northwestern State 64, 3-Seed Iowa 63 (2006)

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AUBURN HILLS, MI - MARCH 17: Jermaine Spencer #1 of the Northwestern State Demons celebrates the 64-63 upset win over the Iowa Hawkeyes in the First Round of the 2006 NCAA Men's Basketball Tournament at The Palace of Auburn Hills on March 17, 2006 in Aub

Down 17 with eight and a half minutes to go, the Demons were dead in the water against the Big Ten tournament champion Hawkeyes. It was time to check out the confections at the Palace of Auburn Hills.

Consecutive threes prompted a quick turnaround. What followed was a frantic comeback that left State down by one as Iowa the final seconds.

Iowa's Greg Brunner missed one of two foul shots in the final seconds, and the Demons had a chance.

Jermaine Wallace rebounded a miss, dribbled to the corner and drained an improbable three-pointer with half of a second left to give Northwestern State the win.

5. 15-Seed Coppin State 78, 2-Seed South Carolina 65 (1997)

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14 Mar 1997: Danny Singletary of the Coppin State Eagles in action during a playoff game against the South Carolina Gamecocks at the Pittsburgh Civic Arena in Pittsburgh, Pennsylvania. Coppin State won the game 78-65.

Using a quote from the Washington Post on March 14, 1997, “This game wasn't expected to be close...and it wasn't."

Coach Ron “Fang” Mitchell's Eagles took a bite out of SEC champion South Carolina that seems to have had a lingering effect.

Coppin State led 55-54 when Danny Singletary made a jumper with just over six minutes to go, and it was lights out for the Gamecocks.

Coming in as 30-point underdogs, the Eagles claimed their first-ever NCAA tournament win.

4. No. 14 Cleveland State 83, No. 3 Indiana 79 (1986)

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4 Apr 1992: Coach Bobby Knight of the Indiana Hoosiers argues with an official during a playoff game against the Duke Blue Devils at the Hubert H. Humphrey Metrodome in Minneapolis, Minnesota. Duke won the game 81-78. Mandatory Credit: Jonathan Daniel

Though Cleveland State won the Association of Mid-Continent Universities (yeah, that title), there was no automatic bid to the tournament.

Instead, the Vikings were given the last at-large bid as a 14-seed. Mind you, they were a 27-3 14-seed.

However, they were going up against Indiana and Bobby Knight.

They ran and pressed and ran some more, disrupting the Hoosiers enough to steal a win, led by Clinton Ransey's 27 points.

3. 15-Seed Santa Clara 64, 2-Seed Arizona 61 (1993)

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BOSTON, MA - MARCH 02: Steve Nash #13 of the Phoenix Suns drives around Kevin Garnett #5 of the Boston Celtics on March 2, 2011 at the TD Garden in Boston, Massachusetts. The Celtics defeated the Suns 115-103. NOTE TO USER: User expressly acknowledges a

This was significant for the upset and the seedings but also for the fact that college basketball fans were exposed to future NBA MVP Steve Nash.

The Santa Clara Broncos were 20-point underdogs against Arizona. The Broncos were as lucky as they were good, surviving a late run of 25 straight points by the fifth-ranked (overall) Wildcats to win, 64-61.

2. 15-Seed Hampton Pirates 58, 2-Seed Iowa State Cyclones 57 (2001)

Brian Bahr/Getty Images

15 Mar 2001: Head Coach Steve Merfeld of the Hampton Pirates pionts from the sidelines during the game against the Iowa State Cyclones at the Boise State Pavilion in Boise, Idaho. The Pirates defeated the Cyclones 58-57.Mandatory Credit: Brian Bahr /All

Tarvis Williams was the hero, scoring with under seven seconds left to lift the Pirates to a one-point win over Iowa State.

The Cyclones led 57-48 with seven minutes left but failed to score a single point the rest of the way.

It was the first victory for Hampton in the NCAA tournament, and for good reason. It was their first appearance.

1. 15-Seed Richmond 73, 2-Seed Syracuse 69 (1991)

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LOUISVILLE, KY - FEBRUARY 12: Jim Boeheim the Head Coach of the Syracuse Orange gives instructions to his team during the Big East Conference game against the Louisville Cardinals at the KFC Yum! Center on February 12, 2011 in Louisville, Kentucky. Loui

The Spiders made history when they became the first 15-seed to win an NCAA tournament game by beating Syracuse, a trend that seems to have some continuity for Richmond.

Richmond led the entire way and made three clutch free throws in the last 21 seconds to seal the deal.

It was the first of only four 15-vs.-2 upsets to date.