Biggest MLB Upsets in History
Baseball has this beautiful way of humbling even the mightiest teams.
You can have the best record, the biggest stars, and all the momentum in the world, and then some scrappy underdog comes along and flips the script entirely.
These moments remind us why we love October baseball so much—anything can happen when the stakes are highest.
Here is a list of 14 of the biggest upsets in MLB history.
1906 World Series
The Chicago Cubs won 116 games during the 1906 season, setting a National League record that still stands today.
They finished with a 116-36 record and a .763 winning percentage, absolutely dominant all year long.
Their opponents, the crosstown White Sox, had earned the nickname ‘Hitless Wonders’ because they batted just .230 as a team during the regular season and finished at .616.
The Cubs should have steamrolled them, but baseball doesn’t always follow the script.
The White Sox won the series in six games, pulling off what remains the largest winning percentage differential upset in World Series history at 147 points.
The 1914 Miracle Braves
On July 4th, 1914, the Boston Braves were sitting in dead last place in the National League, looking like another lost cause.
Then something magical happened—they went on an absolute tear, winning 68 of their final 87 games for a .782 winning percentage.
They caught the New York Giants and won the pennant by 10.5 games.
Nobody gave them a chance against Connie Mack’s Philadelphia Athletics, who featured five future Hall of Famers and had won three of the last four World Series.
The Braves swept them four games to none, outscoring the stunned Athletics 16-6, with pitchers Richard Rudolph and Bill James dominating throughout.
The Associated Press later called it the greatest sports upset of the 20th century in a 1999 retrospective.
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1954 World Series
The Cleveland Indians put together one of the most dominant regular seasons in baseball history in 1954, winning 111 games with a .721 winning percentage.
That mark stood as the best ever for an American League team until matched by the 2001 Mariners.
The New York Giants had won 97 games but were clear underdogs heading into the Fall Classic.
Willie Mays made one of the most iconic catches in baseball history in Game 1, racing back to snag Vic Wertz’s drive over his shoulder at about 425 feet from home plate in the cavernous Polo Grounds.
The Giants swept the Indians in four games, and Cleveland’s powerhouse season ended in stunning fashion.
1960 World Series
The New York Yankees absolutely crushed the Pittsburgh Pirates in terms of overall statistics during the 1960 World Series.
They outscored Pittsburgh 55-27, racked up 91 hits compared to Pittsburgh’s 60, and posted a .338 team batting average.
By all conventional measures, they dominated the series.
But baseball games aren’t decided by aggregate stats—they’re decided one game at a time.
The Pirates won three close games while the Yankees won their games by blowout margins.
Bill Mazeroski’s walk-off home run in the bottom of the ninth inning of Game 7 gave Pittsburgh the championship, and it remains one of the most dramatic endings in baseball history.
The Miracle Mets of 1969
The 1969 Baltimore Orioles were a machine, winning 109 games with stars at nearly every position.
They had Frank Robinson, Brooks Robinson, Boog Powell, and a rotation featuring three 20-game winners in Jim Palmer, Dave McNally, and Mike Cuellar.
The New York Mets were in just their eighth year of existence and had never had a winning season before 1969.
They lost the first game of the World Series, then won four straight to complete the upset.
Tommie Agee made two spectacular defensive plays in Game 3 that saved at least five runs, and the Mets’ pitching staff held the powerful Orioles lineup to a .146 team batting average for the series.
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1988 World Series
The Oakland Athletics came into the 1988 World Series looking unstoppable.
They had won 104 games and featured Jose Canseco (the AL MVP), the best closer in baseball (Dennis Eckersley), and the fastest man in the game (Rickey Henderson).
The Los Angeles Dodgers had Orel Hershiser and an injured Kirk Gibson who wasn’t expected to play.
Then Gibson limped out of the clubhouse in Game 1 and hit one of the most iconic home runs in baseball history, a two-run shot off Eckersley on a 3-2 backdoor slider in the bottom of the ninth to win the game.
Hershiser took over from there, dominating both the NLCS and World Series to earn MVP honors in both, as the Dodgers won the series four games to one.
1990 World Series
The Cincinnati Reds weren’t given much of a chance against the Oakland Athletics in 1990.
The Athletics had the Bash Brothers—Jose Canseco and Mark McGwire—along with Dave Stewart and Dennis Eckersley anchoring the pitching staff.
The Reds came out swinging and never let up, sweeping the heavily favored Athletics in four games.
They beat Stewart 7-0 in Game 1, took down Eckersley in extra innings in Game 2, and completed the sweep with ace José Rijo winning both Games 1 and 4 to earn World Series MVP honors.
2001 ALCS
The Seattle Mariners won 116 games in 2001, tying the all-time record set by the 1906 Cubs.
They had Ichiro Suzuki in his first MLB season, led the majors in runs scored, and dominated from start to finish.
The New York Yankees won 95 games but were clear underdogs based on the regular season records—a 122-point winning percentage differential.
The Yankees won the series in five games, claiming their fourth straight pennant before heading to face Arizona in a classic seven-game World Series.
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2003 Florida Marlins
The Florida Marlins entered the playoffs as a wild card team and weren’t expected to make much noise.
They had fired their manager in May and brought in Jack McKeon, who turned things around dramatically.
The Marlins knocked off the San Francisco Giants in the NLDS, upset the Chicago Cubs in the NLCS, and then defeated the mighty New York Yankees in six games to win the World Series.
Josh Beckett threw a complete-game shutout in Game 6 to clinch the title, making the Marlins just the second wild card team ever to win it all with their 91-71 regular season record.
The 2004 Red Sox Comeback
No team had ever come back from a 3-0 deficit to win a best-of-seven series in baseball history.
The Boston Red Sox were down 3-0 to their archrivals, the New York Yankees, in the 2004 ALCS after getting demolished 19-8 in Game 3.
Dave Roberts stole second base in the bottom of the ninth in Game 4, sparking the most improbable comeback in sports history.
The Red Sox won four straight games, with David Ortiz hitting walk-off hits in Games 4 and 5 to earn ALCS MVP honors.
Johnny Damon hit a grand slam in Game 7 as Boston won 10-3 to complete the comeback, then swept the Cardinals four games to none for their first championship in 86 years.
2006 World Series
The St. Louis Cardinals limped into the playoffs with an 83-78 record, the worst regular season record for a World Series champion in modern baseball history.
The Detroit Tigers had won 95 games and featured seven players with at least 16 home runs, led by Craig Monroe’s 28.
The Tigers had knocked off the Yankees and Athletics to reach the Fall Classic.
The Cardinals upset Detroit in five games, with David Eckstein earning World Series MVP honors despite the team’s underdog status all postseason long.
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2021 NLCS
The Atlanta Braves entered the 2021 playoffs with an 88-73 record, the worst mark of any postseason team that year.
The Los Angeles Dodgers were making their fifth NLCS appearance in six seasons and were heavy favorites at -220 odds.
The Dodgers had to scratch Max Scherzer from his Game 6 start due to a dead arm, which certainly hurt their chances.
The Braves won the series in six games and went on to defeat the Houston Astros four games to two in the World Series, claiming their first championship since 1995.
2022 NLDS
The Los Angeles Dodgers won 111 games in 2022, the highest win total in franchise history dating back to the 1880s.
They won the National League West by 22 games over the San Diego Padres, going 14-5 against them during the regular season.
The Padres had made several blockbuster trades, including acquiring Juan Soto, to try to keep pace.
In the NLDS, San Diego won the series three games to one, completing one of the biggest upsets in modern playoff history with a 136-point winning percentage differential.
The Padres clinched at Petco Park behind Josh Hader’s save.
2023 Postseason Chaos
The 2023 playoffs featured multiple massive upsets that shook up the baseball world.
The Philadelphia Phillies finished 14 games behind the Atlanta Braves in the regular season, then eliminated them in the NLDS for the second straight year.
Both times, the Phillies took Game 1 on the road with strong pitching performances.
The Arizona Diamondbacks pulled off an even more stunning upset, sweeping the 100-win Los Angeles Dodgers in three games at Dodger Stadium despite posting a 7-31 record there since 2019.
Arizona became the first team in postseason history to hit four home runs in a single inning during Game 3 of that series, setting the tone for an October full of surprises.
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When Underdogs Take Over
These upsets have shaped baseball’s October legacy in ways that dominant champions never could.
The 1914 Braves inspired the term ‘miracle’ in sports comebacks.
The 1969 Mets proved expansion teams could win it all in less than a decade.
The 2004 Red Sox showed that no deficit is truly insurmountable when a team refuses to quit.
Each upset added another layer to baseball’s rich tradition of David-versus-Goliath stories, where superior talent and regular season dominance mean nothing once October arrives.
The best team on paper doesn’t always win, and that unpredictability keeps fans coming back year after year, hoping their underdog might be the next to shock the world.
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