The most recent running of the Kentucky Derby was arguably its most controversial. Maximum Security appeared to win the race at 10-to-1 odds, with 65-to-1 long shot Country House finishing second after a late rally.
But the jockeys for Country House and fellow runner Long Range Toddy appealed the result after Maximum Security veered into War of Will. Maximum Security also interfered with Long Range Toddy and Bodexpress. Maximum Security was disqualified and Country House won as the unlikely underdog. The disqualification was the first one to ever change the winning horse due to an on-track infraction in Kentucky Derby history. That makes it one of the biggest sports upsets of all-time, albeit in a strange fashion.
Upset Upsets Man O’ War – 1919 Sanford Memorial Stakes:
If you don’t remember this one, don’t feel too bad. Man o’ War was the most dominant horse in racing throughout his 21-race run from June 1919 to October 1920.
He lost only one race in that timeframe, losing by a mere neck’s length to the aptly named Upset at the 1919 Sanford Memorial from the Saratoga Race Course. Despite the historic upset, Man o’ War rebounded to defeat Upset in his very next race. He then won his next 14 races in a row before retiring as one of the most infamous racehorses in history.
Heading into his match-up with Serra at 2007’s UFC 69, legendary former UFC champion St-Pierre was a nearly spotless 13-1. He had just knocked out the only man to defeat him in MMA, fellow legend Matt Hughes, to win the UFC 170-pound title in his previous bout.
But even though he was a massive dog, Serra didn’t get the memo he was supposed to go down easily. He wobbled St-Pierre with a massive overhand that put him on skates, finishing him off with strikes to complete the jaw-dropping upset victory. The win was so devastating that St-Pierre largely became a wrestling-focused fighter with a penchant for safe, controlling gameplans the rest of his career.
Juan Martin del Potro def. Roger Federer – 2009 US Open:
Federer was simply on fire heading into the 2009 US Open. So much so, in fact, that he was gunning for his sixth consecutive win.
But the No. 6-seeded del Potro took him to the limit, eventually outlasting Federer in the fifth and final set to complete the historic upset. The loss marked a decided down period for Federer, who seemingly couldn’t rekindle his previous magic after this defeat.
VCU def. Kansas – Elite Eight of 2011 NCAA Tournament:
Longtime collegiate basketball juggernauts Kansas Jayhawks are perennial contenders to win the NCAA tournament each March. And 2011 was no different, with the Jayhawks rolling straight through to the Elite Eight as the last No. 1 seed in the tourney.
However, the Virginia Commonwealth University (VCU) Rams weren’t having it. They trounced Kansas 71-61 and found themselves with an unlikely Final Four berth as a result. They also scored one of college basketball’s biggest upsets in the process.
NCAA football superpower USC was a monster favorite heading into their 2007 showdown with Pac-10 opponent Stanford – 41 points, to be exact. But eventual San Francisco 49ers coach Jim Harbaugh took it to Pete Carroll’s Trojans that day.
USC put up a good fight, but ultimately they fell 24-23 when Harbaugh’s team drove down the field for a game-winning score in the fourth quarter. The win will go down in collegiate football history as one of its biggest upsets.
Roberta Vinci def. Serena Williams – 2015 US Open:
Arguably the greatest women’s tennis player of all-time, Williams was on a journey to become the first female since Steffi Graf to lock up a Grand Slam in one year.
That all changed when she met Vinci in the semifinals of the 2015 US Open. There, Vinci outlasted No. 1-ranked Williams in three sets by a score of 2-6, 6-4, and 6-4.
She obviously never became the transcendent star Williams is, but along with partner Sara Errani, Vinci was one of only five couples to complete a career Grand Slam in doubles competition. She’ll always be known for her historic upset of Williams.
Rulon Gardner def. Alexander Karelin – 2000 Summer Olympics:
For many reasons, Karelin was known as the most dominant force in wrestling for many years. Heading into the 2000 Summer Olympics, he had not lost a match in international competition for a resounding 13 (!) years.
That would all change in dramatic fashion, however, when the United States’ Rulon Gardner outlasted him to become one of the most unlikely wrestling medalists of all-time. This one will never go away.
Boise State def. Oklahoma Sooners – 2007 Fiesta Bowl:
This game could legitimately be described as one of the most exciting in college football history.
Known more for their blue home field than actual football prowess, the Boise State Broncos were 7.5-point underdogs to the legendary Oklahoma Sooners heading into the 2007 Fiesta Bowl. Somehow, however, Boise State was able to rack up an 11-point lead at the half. That success was fleeting, as Oklahoma stormed back to take a touchdown lead of their own.
Undeterred, Boise State answered and tied the game. Then, Oklahoma followed right back with another touchdown and went back up. Again the Broncos answered once more, scoring yet again and adding a chance to tie the game. However, what followed went down in NCAA football history. Boise State coach Chris Peterson called the rarely seen Statue of Liberty play to fake out the powerhouse from Oklahoma and win the game in unique fashion. Insane stuff.
Fresno State def. Georgia Bulldogs – 2008 NCAA College World Series:
The Fresno State Bulldogs pulled off one of the most improbable runs in collegiate; no, overall sports history when they won the 2008 NCAA College World Series.
In fact, it’s one of the most unbelievable sporting runs that probably doesn’t receive even close to enough credit for its sheer unlikelihood.
Fresno State had a single NCAA championship in men’s competition before 2008 CWS. Their 1968 men’s tennis team was the only team in school history to win a national championship. Their softball team did win the 1998 NCAA Women’s College World Series.
Fresno State had to win the Western Athletic Conference (WAC) tournament to even get into the CWS. With a record of 33–27, they were not favored to by any means. But they did. Fresno State was then the #4 seed in their regional – the fourth of four. They became the first No. 4 seed to win their way to the College World Series.
Finally, Fresno State faced elimination six times in the NCAA tournament, which included three times in the College World Series. They won all six games, beating six top 20 teams culminating with the massively favored Georgia Bulldogs to win the 2008 CWS. This feat will most likely never be repeated.
Detroit Pistons def. Los Angeles Lakers – 2004 NBA Finals:
The 2003-04 Los Angeles Lakers were supposed to be one of the most stacked teams in NBA history, and on paper, they were.
After dropping their previous playoff run to Western Conference rival San Antonio the previous year, LA went out and signed NBA legend Karl Malone and star point guard Gary Payton. A title seemed like a mere formality for coach Phil Jackson after he added these two stars to his already-formidable duo of Shaquille O’Neal and Kobe Bryant.
Yet this was another “dream team” type of squad that failed to live up the perhaps unattainable hype heaped upon it. Buoyed by the more under-the-radar stars like Chauncey Billups and Ben Wallace, the Detroit Pistons ran over the Lake Show in only five games. This was the only NBA Finals Jackson lost up until that point – he had won all nine of his previous NBA Finals appearances. He retired after the crushing defeat. It was short-lived, of course, but this loss will resonate in NBA history forever.
Kansas City Chiefs def. Minnesota Vikings – Super Bowl IV in 1970:
Back in these days, the AFL was still the underdog to the more established NFL before the two leagues eventually merged, and Super Bowl IV was no different.
The Kansas City Chiefs took on the highly favored Minnesota Vikings as 12.5 to 13-point underdogs. Those betting lines proved to be a fool’s errand. Faced with wet, sloppy conditions, the Chiefs trounced the favored Vikings 23-7 on the heels of three interceptions, and two fumble recoveries. Kansas City also held the Vikings to only 67 rushing yards. Legendary coach Hank Stram gave the Chiefs their only Super Bowl victory, as they haven’t won a Lombardi Trophy since. They are favored to contend for it again this year, however.
Pittsburgh Pirates def. New York Yankees – 1960 World Series:
It’s safe to say the 1960 Worlds Series will go down as one of the most unique instances of the Fall Classic. The favored Yankees scored 55 runs during the series to set the record for most runs by any one team in World Series history. But they didn’t win the series.
The Yankees won three games by massive margins of 16–3, 10–0, and 12–0. The Pirates, however, won four nail biters by the scores of 6–4, 3–2, 5–2, and 10–9 to steal the series. Bill Mazeroski ended the legendary win with a ninth-inning home run in game seven. It was the only time a walk-off homer ended a season-ending title game.
Bobby Richardson of New York was named the MVP; the only time the award has been handed to a player who wasn’t on the winning team. Strange stuff of legends.
For a while in the fateful fall of 2003, it looked like the Chicago Cubs were finally going to break their painful curse. They were the odds-on favorite to win the World Series, and they started the playoffs living up to that billing.
Winning their way to the National League Championship Series, Chicago held a 3-2 series lead on the Florida Marlins prior to a potential clinching game 6. They even managed to maintain a 3-0 lead in the eighth inning, but then one of the most infamous moments in the Cubs’ history happened. A foul ball sailed towards the stands, with Cubs player Moises Alou attempting to track it. Ostracized Cubs fan Steve Bartman reached out to grab the ball to Alou’s protest. It’s highly debatable if he would have been able to catch it. But he did not, and the tide had turned.
The floodgates opened with Florida putting eight runs on the board in that insane inning alone. Of course, they won that game and the game 7 that followed to shut down the Cubs’ run to the title. The Marlins went on to score eight runs that inning, and would eventually win Games 6 and 7. Their already brutalized fanbase was heartbroken, but thankfully the Cubs finally won the title again in 2016.
Robin Soderling def. Rafael Nadal – 2009 French Open:
Tennis fans know that Nadal is the king of the clay court. So much so that he was attempting to win his fifth straight French Open when he met 23rd-seeded Soderling in the third round of the 2009 iteration of the Open. To put this match in context, Soderling had never won such a match in a major in his career.
But he did against Nadal by defeating the dominant star with a score of 6-2, 6-7 (2-7), 6-4, 7-6 (7-2). The match was one of the more shocking defeats in French Open – and tennis overall – history.
New York Mets def. Baltimore Orioles – 1969 World Series:
The infamous “Miracle Mets” completed their unlikely rise to legendary status in the 1969 World Series. Facing a vaunted Baltimore team that had amazing pitchers and was dubbed one of the best of all-time, the eight-year-old Mets remained unfazed.
Trouncing the Orioles in only five games, the Mets became the first expansion team to win a World Series. The Arizona Diamondbacks and Florida Marlins won the World Series faster, but the 1969 “Miracle Mets” will always be the first.
There’s not much else to say about this one other than Rousey was a bulldozer trouncing everyone before Holm stopped her right in her tracks. Rousey had finished opposition with ruthless ease and efficiency during her run as UFC women’s bantamweight champion.
That all came crashing down when Holm outclassed her in the stand-up at UFC 193, however. A vicious head kick landed clean and Rousey’s title reign was over then and there. Her entire mixed martial arts career essentially was, too. She fought once more and was finished by Amanda Nunes in 48 seconds before leaving the UFC for good and going to the WWE.
Soccer has never been exactly the United States’ area of expertise in sporting prowess, as the rest of the world tends to outpace them quite handily on the pitch. Indeed, they had lost 45 of their last 47 games internationally before this historic match-up.
Of course, Great Britain had always been one of the world-class teams ranked higher than the Americans. Heading into the 1950 World Cup, England was a monstrous 500-to-1 favorite over America. The US shocked them by a score of 1-0, however.
The famed Hoyas came into the 1984-1985 season the favorites to take it all again as the defending national champions. It was all playing out to the plan, too, as they made the tourney as the No. 1 team in the nation and the No. 1 seed. Their success continued into the Final Four.
Faced with the task of Rollie Massimino’s No. 8 seed Villanova Wildcats in the finals, the Georgetown Hoyas fell one game short that season. The Cats shocked them by a close margin of 66-64, shooting an unreal shooting percentage from the floor to do so and score one of college basketball’s biggest upsets.
Arizona Diamondbacks def. New York Yankees – 2001 World Series:
Like the aforementioned 1969 Mets, the Diamondbacks were an expansion team looking to win the World Series only a few years into their existence. They accomplished the task in half the time it took the legendary “Miracle Mets.”
And they beat the New York Yankees to do it. But not without a lot of drama, as New York had them down 2-1 in Game 7 of the series. Legendary reliever Mariano Rivera was on the mound and it appeared bad. But Luis Gonzalez hit a fateful shot up the middle to steal the World Series, giving them a title only four years after they debuted in MLB.
Legendary coach John R. Wooden led the Bruins to the most dominant NCAA basketball run in history. Having secured an unreal seven straight national titles, UCLA also won 88 straight games from 1971-74.
Yet the run came crashing down when they battled Notre Dame in 1974. The Bruins would go on to lose four games that season. It was a letdown that they only finished third in the NCAA that year, a testament to their greatness.
Leicester’s Premier League win in 2016 might go down as one of the biggest feel-good stories in all of sports and definitely in soccer. The team was 5000-1 to win before the 2015-2016 year.
Those unreal odds didn’t mean a thing when they took home the title on May 2, 2016, however. Riyad Mahrez was named the PFA Players’ Play Of The Year. He became the first African player to win that coveted honor. Striker Jamie Vary also set the Premier League’s record for most goals scored in back-to-back games, sending Leicester City to their first UEFA Champions League play in 2016-2017.
‘The Greatest’ expected an easy bout from relative newcomer Spinks in 1978, as Spinks had only seven professional bouts heading into his showdown with Ali. He shocked the boxing world by out-boxing Ali over the course of 15 rounds to win a decision.
Spinks did not tire throughout the fight even though it was far from easy. He became the only man to take the title from Ali. The legendary boxer had only lost fights where he was challenging for the belt or non-title bouts. Spinks was later stripped of his WBC title for refusing to defend it against Ken Norton, instead facing Ali in a rematch for the WBA belt. This time ‘The Greatest’ came prepared and won by unanimous score. But Spinks’ first win over Ali remains one of the biggest upsets in boxing history.
The lesser-known George Mason University in Fairfax, Virginia, isn’t discussed as an NCAA basketball powerhouse. But that was indeed the case in 2006 when they somehow made not only the NCAA tournament but also the Final Four.
To get there, they somehow toppled 5 Michigan State, No. 3 North Carolina, No. 7 Wichita State and No. 1 UConn in one of the most stunning runs in NCAA sporting – not just basketball – history. They would lose to eventual national champ Florida, but that doesn’t take away from this historic upset.
George Mason’s aforementioned Final Four run was an unreal run, but George Foreman’s improbably heavyweight title run was an all-time upset by a George of a different kind.
Still competing at 45 years old, Foreman had lost his previous bout to Tommy Morrison and was in no position to receive a title shot. He did due to his lengthy resume and name recognition, however, facing Michael Moorer on November 5, 1994.
19 years the junior to his opponent, Moorer out-boxed Foreman for nine rounds. However, Foreman came alive to land a perfect right on Moorer’s chin. A knockout win followed, and Foreman set some insane records in the process. He became the oldest fighter to win the heavyweight title and set a new record for the longest time in between title runs.
Milan High School def. Muncie Central High School – 1954 Indiana State Basketball Championships:
When they make a movie about an upset, you know it’s a historic win.
It was only high school basketball, but that is life in the State of Indiana. Milan High School fought powerhouse Muncie Central High School in the 1954 State Basketball Championships.
It wasn’t the high-scoring affair that many fans have come to expect from the basketball match-ups of today, but Muncie won 32-30 to the surprise of everyone close to the tourney. The story later became immortalized in the movie ‘Hoosiers’ starring Gene Hackman.
Led by revered coach ‘Tark the Shark’ Jerry Tarkanian, UNLV entered the 1990-1991 season after absolutely demolishing Duke with a score of 103-73 in the 1990 NCAA Tournament Finals. They finished the 1990-1991 regular season unbeaten at 27-0 and won their way to the Elite Eight of the tourney.
They had won 45 straight games before the met Duke yet again. But this time around, the Blue Devils got revenge with a 79-77 win, snapping UNLV’s run before winning the title in the next game.
This comeback will forever reign in the history of the MLB. Without a title in 86 years, the Red Sox’ hopes were high in the 2004 playoffs. But they promptly fell behind three games to none in the American League Championship Series (ALCS) to their AL East and heated rivals, the New York Yankees.
Boston didn’t give up, taking the next four games in one of the most unbelievable comebacks in sports history. Other (albeit few) teams had come from three-game deficits to win seven-game series, but the Red Sox’ win was more important. They snapped their long cold streak by beating the Cardinals to win the World Series.
Texas Western def. Kentucky – 1966 NCAA Tournament Finals:
Texas Western’s 1966 NCAA Championship victory changed the face of college basketball forever.
Coach Don Haskin’s Miners were the first team with an all-black starting five to win an NCAA Tournament. Perhaps more importantly, the topped the longtime powerhouse Kentucky Wildcats in a legendary final 72-65 from College Park that spring. Kentucky was a team that had been all white up until 1969. The huge upset opened a path for African-American athletes in collegiate sports and was remembered in both the book and film “Glory Road.”
North Carolina State def. Houston – 1983 NCAA Tournament Finals:
Jim Valvano’s NC State was an underdog long before they faced juggernaut Houston in the NCAA tournament finals in 1983. After an injury to star Derrick Whittenburg forced the Wolfpack to a No. 4 finish in the ACC, NC State needed to win the ACC tourney to even get into the NCAA tournament. Somehow, they beat the favored North Carolina Tar Heels led by one Michael Jordan and made it.
They fought their way to the title game against Houston, who boasted stars Hakeem Olajuwon and Clyde Drexler. No one believed NC State could top “Phi Slama Jama’s” style of fast-paced offense. But they did in one of college basketball’s all-time greatest games, scoring a 54-52 victory when a Whittenburg miss was slammed home by Lorenzo Charles. It will remain one of the most iconic images in college basketball, along with late Valvano rushing onto the court to celebrate.
New York Giants def. New England Patriots – Super Bowl XLII in 2008:
The 2007 version of the New England Patriots was the most dominant regular season team in NFL history. They destroyed every team on their way to a perfect 16-0 mark, with Tom Brady setting the NFL record for most touchdown passes in a single regular season.
The Patriots went into Super Bowl XLII as monstrous 12-point favorites over the opposing New York Giants. True, it took a lucky catch from wideout David Tyree where he held the ball against his helmet and a last-minute touchdown pass from Eli Manning to Plaxico Burress, but they shocked the entire world. Their defensive pressure of Brady was also an unsung reason why they could hold New England to only 14 total points. And like that, the Pats’ shot at perfection was sent down the drain.
Here we could have the biggest upset in the history of NCAA football. The Michigan Wolverines were deservedly 27-point favorites when they welcomed FCS team Appalachian State to their revered Big House.
Although The Mountaineers would win the FCS national title that year, they were still predicted to get smoked by the Wolverines. That did not transpire. Appalachian State picked up a 34-32 win to shove everyone watching’s jaws to the ground.
When WBA (Super)/WBO/IBF/IBA heavyweight champion Anthony Joshua’s original opponent Jarrell Miller fell through due to multiple failed drug tests, 32-1 Ruiz Jr. put his name into the running with Joshua’s promoter Eddie Hearn. He got the fight and soon made history.
Despite the portly Ruiz Jr. facing -2500 favorite Joshua, he became the first-ever Mexican heavyweight champion in one of the most shocking performances of all-time. Ruiz Jr. was floored early but finished the chiseled Joshua via TKO in the seventh round to steal the belts. He’s expected to rematch Joshua later this year.
Denver Nuggets def. Seattle Supersonics – 1994 NBA Playoffs:
The Seattle Supersonics were viewed as one of the favorites to win the NBA title in 1994. Boasting stars Gary Payton and Shawn Kemp, they had bulldozed through the season. They came into the playoffs as the No. 1 seed in the Western Conference and played the No. 8-seeded Denver Nuggets in the first round. Things were going along according to plan and they won the first two games of their best-of-five series.
But Denver somehow came back to win an unreal three games in a row, sparking one of the biggest upsets in NBA history. Their unsung group of heroes such as Robert Pack, Reggie Williams, and Brian Williams all put in their best showings to force overtime in the fifth and deciding game. They won 98-94, and the iconic image of Denver star Dikembe Mutombo celebrating in elation will last forever. They became the first No. 8 seed to beat a No. 1 seed.
UMBC def. University of Virginia – First Round of 2018 NCAA Tournament:
Like the Denver Broncos back in 1994, the UMBC Retrievers made history in men’s basketball, but this time in the NCAA tournament. The University of Virginia was seeded first overall in the NCAA Tournament. They were the No. 1 seed in the South Regional and met No. 16 seed UMBC in the opening round.
UMBC made history by defeating UVA by a lopsided score of 74–54. It wasn’t all that close. It was also their first-ever NCAA Tournament win. They became the first No. 16 seed to defeat a No. 1 seed in the men’s NCAA Tournament.
New York Jets def. Baltimore Colts – Super Bowl III in 1969:
There are few more iconic upsets than the one that took place at Super Bowl III in 1969. Of course, that was where ‘Broadway’ Joe Namath guaranteed his team would top the favored Colts in the game, and they did.
It wasn’t too pretty. The Jets won by a score of 16-7 thanks to a single touchdown run and three field goals. Namath went 17-of-28 passing for 206 yards. Of course, he was named the game’s most valuable player. He was the first player to win the award at the Super Bowl without accounting for a touchdown for his team. The Jets defense may have been the unsung heroes of the game, as they picked off Colts quarterback Earl Morrall three times to help seal the win. But it was and will be Namath’s guarantee of victory that will go down in NFL history.
Buster Douglas Knocks Out ‘Iron’ Mike Tyson – 1990:
There’s no denying that Andy Ruiz Jr.’s knockout of Anthony Joshua was a shocking spectacle to say the least. However, there’s just not another boxing upset that could top this one. Mike Tyson met Buster Douglas, in Tokyo on February 11, 1990. ‘Iron’ Mike was unbeaten and a feared a boxer as there ever was. He had dominated the heavyweight division for three years prior. His fight with Douglas was largely thought of as a mere setup fight for a showdown with the also-undefeated Evander Holyfield.
So no one gave 42-to-1 dog Douglas much of a chance. How could they have, really? Douglas controlled the action from the outset, peppering Tyson with endless jabs. The strikes took their toll and Tyson’s eye began to sell shut, something his corner was not prepared for. Tyson knocked Douglas down in the eighth round, but Douglas came back. He landed a ton of damage in the ninth round and Tyson was in trouble heading into the tenth. A monster uppercut rocked Tyson, and a four-punch combo sealed the deal for the biggest upset in boxing history.
United States def. Russia – 1980 Winter Olympics Hockey Semifinals:
There just is no other upset that could be listed number one on this list. This is the upset in sports history.
The Russian team was heavily favored to win the gold heading into the 1980 Winter Olympics from Lake Placid, New York, and for good reason. The Russians won five of the six previous Olympic gold medals in ice hockey. They met up with the much less experienced U.S. team in the semifinals.
What happened there was sports history in the fullest sense. The Americans, facing a 3-2 deficit heading into the final period, put two goals on the board to emerge with the miraculous 4-3 victory. The win became known as the iconic ‘Miracle on Ice’ and will almost certainly be the biggest sports upset of all-time for the rest of time.