How Well Do You Know the Greatest Upsets in US Pro Sports History?

By: Gavin Thagard
Estimated Completion Time
5 min
How Well Do You Know the Greatest Upsets in US Pro Sports History?
Image: Wikicommons by Wikicommons by Keith Allison from Hanover, MD, USA

About This Quiz

The odds have been put out, and the bets are in. Everyone's sure the heavily favored team is going to come through because they've been playing at a high level all season, and they have a roster stacked with talent from top to bottom. There's one thing standing in their way, though — the team on the opposite side of the field who has plans to derail their season with a win of their own.

There's nothing quite like an underdog story in sports, where David faces off against Goliath in what seems like an impossible matchup. When the underdog comes through, it's not only shocking but inspirational. It has the potential to captivate an entire fanbase while sinking another. Hundreds of articles and stories are written about it, and the heroics of the underdog get more and more extravagant with every story that's told.

Are you ready to test your knowledge of these major upsets that defined U.S. sports? From boxers getting knockouts that no one saw coming to teams making historic comebacks to win a series they weren't supposed to win in the first place, this quiz covers it all. 

When you're ready, show off your sports knowledge by winning the upset over this quiz.

Question 1 - Jets
Wikicommons by Keith Allison from Hanover, MD, USA
Do you know which player from the New York Jets guaranteed a victory against the heavily favored Baltimore Colts before delivering on his promise in Super Bowl III?
Matt Snell
Joe Namath
George Sauer Jr.
Bill Mathis
Correct Answer
Wrong Answer

Throwing more interceptions than touchdowns during his Super Bowl-winning season, Joe Namath was far from the greatest quarterback to play, even for his era. However, he did just enough in the championship game to get the victory and take home the Super Bowl MVP.

Question 2 - Los Angeles Lakers
Wikicommons by scott mecum
The Los Angeles Lakers had Kobe Bryant and Shaquille O'Neal when which team took them down in the 2004 NBA Finals?
Correct Answer
Wrong Answer

The Los Angeles Lakers had one of the most high-powered offenses in the league in the 2003 - 2004 season, and the Detroit Pistons relied on their defense to win games. That defense came through in the finals, as the Pistons held the Lakers to under 100 points every game in the series.

Question 3 - Mets
Wikicommons by Joe_Pignatano,_Eddie_Yost,_Yogi_Berra_1969.jpeg: Peter Manzari from Bayside, NYC, USAderivative work: Delaywaves talk
What name was given to the 1969 New York Mets team that won a World Series after posting the first winning record in franchise history?
Miracle Mets
Marching Mets
Mayhem Mets
Moody Mets
Correct Answer
Wrong Answer

The 1969 MLB season began the divisional era in the majors, as the 24 teams were divided into four divisions between two leagues. This change benefited the New York Mets, who won the NL East with a record of 100-62.


Question 4 - Superbowl 4
Despite being heavily favored, the Minnesota Vikings lost to the Kansas City Chiefs in Super Bowl IV. Where did the game take place?
Los Angeles
San Diego
New Orleans
Correct Answer
Wrong Answer

Viewed as an inferior league, no one thought the AFL would defeat the NFL in a Super Bowl two years in a row, but the Kansas City Chiefs had other plans. After scoring the first points in the first quarter, they never looked back, maintaining the lead throughout the entire game.

Question 5 - Tyson
Mike Tyson's tear through the heavyweight division came to an end in 1990 when he was knocked out in which round by another American fighter, Buster Douglas?
Correct Answer
Wrong Answer

Mike Tyson was 37-0 when he went into the matchup against Buster Douglas in 1990. However, while he was still dominating in the ring, his life outside the ring was in turmoil, as he struggled both with his management while also going through a divorce. With his head elsewhere, Tyson suffered one of the most surprising losses in sports history.

Question 6 - Cavs
Wikicommons by Keith Allison
How far down in the series were the Cleveland Cavaliers in the 2016 NBA Finals when they came back to defeat the Golden State Warriors?
Correct Answer
Wrong Answer

The Cleveland Cavaliers went into the 2016 NBA Finals having lost the previous season to the Golden State Warriors. During the 2015-16 season, the Warriors only improved from the year before, posting a historic 73 wins. LeBron James and the Cavaliers wouldn't be denied a championship, though.


Question 7 - Twins
Who was awarded the series MVP when the Minnesota Twins defeated the Detroit Tigers in the 1987 ALCS?
Gary Gaetti
Tom Brunansky
Greg Gagne
Frank Viola
Correct Answer
Wrong Answer

Founded in 1901 as the Washington Nationals, the Twins made the move to Minnesota in 1961 and were still in search of their first championship when 1987 rolled around. Despite a regular season where they only won 85 games, the Twins fought their way through the playoffs to bring a title to Minnesota.

Question 8 - Federer
Wikicommons by Mike McCune from Portland
On what type of court did Roger Federer fail to win his sixth title in a row at the 2009 U.S. Open?
Clay court
Hard court
Grass court
Carpet court
Correct Answer
Wrong Answer

Roger Federer was on his way to winning his third major of 2009 when his hopes were crushed by Juan Martin del Potro. In a match that seemed to go on forever, del Potro finally took Federer down after five sets.

Question 9 - Pats
Wikicommons by SAB0TEUR
The New England Patriots came into Super Bowl XLII with how many losses on their resume that season?
Correct Answer
Wrong Answer

When the New England Patriots entered Super Bowl XLII, they were the first team in NFL history to record an 18-0 record, as the Miami Dolphins only played 17 games when they went undefeated in 1972. However, their hopes of making NFL history ended on a miracle play by Eli Manning, as the New York Giants came out victorious.


Question 10 - Denver Nuggets
Do you know what seed the Denver Nuggets were when they took down the Seattle SuperSonics in the 1994 NBA Playoffs?
Correct Answer
Wrong Answer

Led by the defensive dominance of Dikembe Mutombo, the Denver Nuggets became the first eighth seed in NBA history to take down the first seed in the playoffs when they accomplished the feat in 1994. Of course, it took all five games of the series and two overtime victories to get it done.

Question 11 - Pirates
Wikicommons by Pittsburgh Pirates / Major League Baseball
In the 1960 World Series, which went all seven games, the New York Yankees lost four close games to the Pittsburgh Pirates. How did Game 7 end?
Walk-off run on a ground ball
Walk-off home run
Tag out at second base
Correct Answer
Wrong Answer

If you look at the statistics, it's hard to see exactly how the Pittsburgh Pirates beat the New York Yankees in the 1960 World Series. After all, the Yankees scored 28 more runs than the Pirates in the series. But the Pirates did just enough to get four victories and take the series with a walk-off home run in Game 7.

Question 12 - Jones Jr
What year did Antonio Tarver knock out Roy Jones Jr. after losing to him sixth months earlier?
Correct Answer
Wrong Answer

Roy Jones Jr. was one of the rare fighters who held championships in four different weight classes, moving from middleweight to heavyweight in his boxing career. When he lost to Antonio Tarver in 2004, he also lost the WBA, WBC, IBO and "The Ring" light heavyweight titles.


Question 13 - Dolphins
Wikicommons by Chris J. Nelson
Can you name the rookie quarterback for the Miami Dolphins who lost to the Seattle Seahawks in the divisional round of the 1983 - 1984 playoffs?
Doug Flutie
Troy Aikman
Jim Kelly
Dan Marino
Correct Answer
Wrong Answer

Despite being one of the best regular season quarterbacks in NFL history — even making his way into the Hall of Fame — Dan Marino failed to get it done in the playoffs. In fact, he's often regarded as the best quarterback to never win a Super Bowl.

Question 14 - Orel
Wikicommons by jimmyack205
Identify the regular-season award Orel Hershiser won in 1988 before helping the Los Angeles Dodgers defeat the Oakland Athletics in the World Series.
Hank Aaron Award
Cy Young Award
Silver Slugger Award
Correct Answer
Wrong Answer

Orel Hershiser's 1988 season was one of the best in baseball history, as he led the National League in wins to earn the NL Cy Young Award. However, his playoff run was even better, winning a World Series while also being named the NLCS MVP and World Series MVP.

Question 15 - Heat
Wikicommons by Keith Allison
Are you familiar with the team that took down the Miami Heat in the 2011 NBA Finals even though the Heat had stars like LeBron James and Dwyane Wade?
Correct Answer
Wrong Answer

Dirk Nowitzki, the star player for the Dallas Mavericks, just wouldn't be denied during the 2011 NBA Playoffs. Even before taking down the Miami Heat, Nowitzki led the Mavericks past the two-time defending champion Los Angeles Lakers and the Oklahoma City Thunder, who had two stars of their own.


Question 16 - Nicklaus
Wikicommons by pocketwiley
Well past his prime, how old was Jack Nicklaus when he surprised the golf world by winning the 1986 Masters Tournament?
Correct Answer
Wrong Answer

There was no questioning Jack Nicklaus' greatness when he entered the 1986 Masters Tournament, but no one expected him to come away with another win, as he hadn't won a major since 1980. However, with the victory, he obtained his 18th major championship, the most all-time.

Question 17 - Bills
Wikicommons by Erik Drost
The Buffalo Bills lost four straight Super Bowls in the early '90s, but they never came closer to winning than in Super Bowl XXV, where they were favored by seven over the New York Giants. What was the final score of that game?
Correct Answer
Wrong Answer

Super Bowl XXV came down to the final seconds of the game, as the Buffalo Bills had an opportunity to score with just over two minutes remaining in the game. They got in position for a 47-yard field goal, but Scott Norwood missed it..

Question 18 - Magic Johnson
Despite Earvin "Magic" Johnson winning the NBA MVP in 1990, why didn't the Los Angeles Lakers make the NBA Finals for the second year in a row?
They didn't make the playoffs.
They lost in the first round.
They lost in the conference semifinals.
They lost in the conference finals.
Correct Answer
Wrong Answer

The Los Angeles Lakers had not only the league MVP but also the best record in the Western Conference coming into the 1990 NBA Playoffs. However, they weren't ready for the Phoenix Suns in the conference semifinals, losing the series in only five games.


Question 19 - Marlins
Wikicommons by Cathy Taylor
After four straight losing seasons, no one expected the Florida Marlins to beat the Atlanta Braves in the NLCS to advance to the World Series. Who was awarded the NLCS MVP for helping the Marlins secure the series?
Livan Hernandez
Moises Alou
Gary Sheffield
Kevin Brown
Correct Answer
Wrong Answer

Livan Hernandez played in two games in the 1997 NLCS, earning victories in both of them while recording a 0.84 ERA. Pitching just over 10 innings in the series, Hernandez had 16 total strikeouts, including a record 15 in Game 5.

Question 20 - UFC 69
Coming into UFC 69, Georges St-Pierre was expected to defeat Matt Serra easily, but Serra came away with a TKO victory. Where did this fight take place?
New York
Las Vegas
Los Angeles
Correct Answer
Wrong Answer

Having just won the UFC Welterweight Championship against Matt Hughes, Georges St-Pierre had only one loss on his resume coming into his matchup in Houston against Matt Serra. A lack of focus led to St-Pierre getting caught in the first round, and the match was called at the 3:25 mark.

Question 21 - Jags
Wikicommons by Craig ONeal
How long had the Jacksonville Jaguars been playing games in the NFL when they defeated John Elway and the Denver Broncos to advance to the 1996 - 1997 AFC Championship Game?
One year
Two years
Three years
Four years
Correct Answer
Wrong Answer

After going 4-12 in their first NFL season, the Jacksonville Jaguars improved to 9-7 in their second year making the NFL Playoffs as a Wild Card team. The Denver Broncos, on the other hand, had gone 13-3 during the 1996-97 season, but that record didn't matter when the Jaguars showed up to Mile High Stadium.


Question 22 - 76ers
Wikicommons by Keith Allison
Coming into the 1984 NBA Playoffs as the defending champions, the Philadelphia 76ers fell to what team in the first round?
Correct Answer
Wrong Answer

The Philadelphia 76ers went 12-1 in the 1983 NBA Playoffs to take home the championship. They returned many of the same stars from the previous year, including Moses Malone and Julius Erving, but it wasn't enough to get the 76ers back to the NBA Finals, as they lost in the first round to the New Jersey Nets.

Question 23 - Serena Williams
Wikicommons by Tatiana from Moscow, Russia
Failing to win her fourth straight title at the U.S. Open, when did Serena Williams lose to unseeded Roberta Vinci in 2015?
First round
Correct Answer
Wrong Answer

Roberta Vinci's victory over Serena Williams in the 2015 U.S. Open denied Williams the opportunity to win all four major tournaments in a calendar year. It was the second time in Williams' career that she won three major tournaments without capturing the fourth.

Question 24 - Marlins
Who led the Florida Marlins to a World Series championship in 2003 after the team fired former manager Jeff Torborg?
Jack McKeon
Joe Torre
Mike Scioscia
Dusty Baker
Correct Answer
Wrong Answer

Jeff Torborg was in his second season with the Florida Marlins when the team started the 2003 season off with a 16-22 record, which led to his firing. Under Jack McKeon, the Marlins made a comeback to finish second in the NL East with a 91-71 record. They went on to beat the New York Yankees in the World Series.


Question 25 - Rams
Wikicommons by GMO66. Cropped by User:Blueag9
Do you know the name of the St. Louis Rams' high-powered offense that lost to the New England Patriots in Super Bowl XXXVI?
Cardiac Rams
The Dream Team
The Greatest Show on Turf
The Triplets
Correct Answer
Wrong Answer

"The Greatest Show on Turf" was led by quarterback Kurt Warner and running back Marshall Faulk. Both players came into Super Bowl XXXVI with NFL MVPs on their resume, Warner having won two and Faulk with one. But their individual accolades weren't enough to take down the New England Patriots in the championship game.

Question 26 - Trail Blazers
Wikicommons by Sport Magazine
The Portland Trail Blazers took home the 1977 NBA championship by winning how many games in a row to finish the series?
Correct Answer
Wrong Answer

The one player the Philadelphia 76ers couldn't account for in the 1977 NBA Finals was Bill Walton, who had the greatest series of his career. After averaging 18.5 points and 19 rebounds per game, Walton was named the MVP of the series.

Question 27 - De La Hoya
Competing at the MGM Grand Garden Arena in Nevada, which boxer upset Oscar De La Hoya in the final boxing match of his career?
Floyd Mayweather Jr.
Manny Pacquiao
Bernard Hopkins
Shane Mosley
Correct Answer
Wrong Answer

Manny Pacquiao was already an established fighter when he went up against Oscar De La Hoya, but he hadn't fought in the welterweight division before the fight. The added size didn't matter as Pacquiao defeated his opponent in the eighth round.


Question 28 - Lynch
Wikicommons by Mike Morris
In a play known as "The Beast Quake," Marshawn Lynch ran 67 yards for a touchdown in the 2010 - 2011 NFC Wild Card Game to help the Seattle Seahawks secure the victory over what team?
Correct Answer
Wrong Answer

Marshawn Lynch joined the Seattle Seahawks in the middle of the 2010 season after he was traded from the Buffalo Bills. When the Seahawks reached the playoffs, it was Lynch's first postseason game, and he didn't disappoint, rushing for 131 yards and a touchdown.

Question 29 - Curt Schilling
Wikicommons by Googie man
Identify Curt Schilling's article of clothing that was soaked in blood when he helped the Boston Red Sox win Game 6 of the 2004 ALCS.
His jersey
His pants
His sock
His hat
Correct Answer
Wrong Answer

The New York Yankees were up 3-0 in the 2004 ALCS when the Boston Red Sox launched one of the greatest comebacks in baseball history to take down their longtime rival in seven games. One of the most famous games in the series was Game 6, known as "The Bloody Sock Game" because Curt Schilling continued pitching as his ankle bled out.

Question 30 - Durant
Wikicommons by Cyrus Saatsaz
Kevin Durant suffered which injury that gave the Toronto Raptors enough life to win the 2019 NBA Finals?
Achilles tear
Torn ACL
Torn pectoral muscle
Broken ankle
Correct Answer
Wrong Answer

The Golden State Warriors came into the 2019 NBA Finals as back-to-back NBA champions, and they were poised to win another title with a roster stacked with talent. However, injuries decimated the team during the NBA Finals, as both Kevin Durant and Klay Thompson went down in the series.


Question 31 - Andrea
Andrea Jaeger was at the height of her career when she entered the U.S. Open in 1981. However, she suffered a major upset in the second round against what player?
Julie Harrington
Renee Richards
Paula Smith
Andrea Leand
Correct Answer
Wrong Answer

Andrea Jaeger's loss in the 1981 U.S. Open was stuffed between two years during which she made the semifinals in the tournament. Despite reaching No. 2 in the rankings in 1981, she never captured a major and was forced to retire in 1985 due to injuries.

Question 32 - Flacco
Wikicommons by Keith Allison
What position did Joe Flacco play when he helped the Baltimore Ravens reach Super Bowl XLVII, which included a victory over the favored Denver Broncos in the divisional round?
Running back
Wide receiver
Defensive end
Correct Answer
Wrong Answer

After finishing 8-8 in the 2011 - 2012 season, the Denver Broncos added Peyton Manning to their roster and improved to 13-3 the following year, finishing first in the AFC. Their first-round bye in the 2012 - 2013 NFL Playoffs didn't help any, though, as the Baltimore Ravens pushed them to two overtimes before claiming victory in the divisional round.

Question 33 - Wilt Chamberlain
Wikicommons by Fma12
After adding Wilt Chamberlain, the Los Angeles Lakers were finally supposed to overcome the Boston Celtics in the 1969 NBA Finals, but they still went down in how many games?
Correct Answer
Wrong Answer

The Los Angeles Lakers came into the 1969 NBA Finals having already lost five times in the finals to the Boston Celtics during the decade. But in 1969, the Celtics were on the decline, and the Lakers had three stars in Jerry West, Wilt Chamberlain and Elgin Baylor. Still, these Hall of Famers didn't have enough to topple Bill Russell and the Celtics.


Question 34 - Cubs
Wikicommons by Arturo Pardavila III from Hoboken, NJ, USA
The Chicago Cubs were MLB's ultimate underdog when they finally won the World Series in 2016 after not winning a championship since when?
Correct Answer
Wrong Answer

The Chicago Cubs championship drought, which lasted from 1908 until 2016, was the longest in Major League Baseball at the time. During the 2016 World Series, it looked like the Cubs were going to disappoint fans again after starting the series 3-1, but they won three games in a row to claim the title over the Cleveland Indians.

Question 35 - Royce Gracie
Wikicommons by
The entire fighting world was stunned when Royce Gracie won UFC 1. Where was the tournament held?
New York
Correct Answer
Wrong Answer

UFC 1 was much different than it is today, as it was a tournament-style competition that didn't have weight classes. When the tournament began, no one expected the undersized Royce Gracie to come out with the win, but his Brazilian jiu-jitsu was too much for the other competitors to overcome.

You Got:
Wikicommons by Wikicommons by Keith Allison from Hanover, MD, USA