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The World Series is the annual postseason conclusion to America’s pastime. In its best-of-seven format, tension is felt in the moments between every pitch, and fans of the sport hold their breath on each offering from the pitcher, whether it’s the first inning of Game 1 or the potential final out in a decisive Game 7. The crack of the bat and pop of the glove never sound as crisp as they do in late October during the Fall Classic, and neither sound is more memorable than amid an all-time series upset.
Here are the top five biggest upsets in World Series history.
The 1906 World Series saw the “Hitless Wonders” Chicago White Sox face off against the heavily favored Chicago Cubs, who had won 116 games that season (remains tied for the regular season record with the 2001 Seattle Mariners). The Cubs were expected to dominate due to their superior regular-season record and well-rounded roster.
However, the White Sox, known for their weak hitting (.230 team batting average), surprised everyone with timely hitting and stellar pitching. They won the series in six games, marking one of the earliest and biggest World Series upsets.
The 1960 World Series featured the Pittsburgh Pirates against the New York Yankees, who had outscored the Pirates 55-27 in the series. Despite being heavily outperformed statistically, the Pirates managed to push the series to seven games.
The decisive Game 7 is remembered for Bill Mazeroski’s walk-off home run, the first and only one to end a World Series Game 7. The Pirates’ unlikely victory over the powerhouse Yankees remains one of the biggest World Series upsets in history.
In 1988, the Los Angeles Dodgers faced the Oakland Athletics, who were considered the best team in baseball. The A’s had a powerful lineup and strong pitching, while the Dodgers were seen as a light-hitting team, especially without their injured MVP Kirk Gibson.
However, Gibson’s iconic pinch-hit walk-off home run off Dennis Eckersley in Game 1 set the tone for the series. The Dodgers, led by Orel Hershiser’s dominant pitching, won the series in five games, pulling off one of the biggest World Series upsets ever.
The 2001 World Series had the Arizona Diamondbacks, in just their fourth year of existence, taking on the three-time defending champion New York Yankees. The Yankees, with their postseason experience, were favored to win.
However, the Diamondbacks, led by the formidable pitching duo of Randy Johnson and Curt Schilling, pushed the series to seven games. In a thrilling Game 7, Luis Gonzalez hit a walk-off single against Mariano Rivera, securing a dramatic and unexpected victory for the Diamondbacks.
The 2006 World Series saw the St. Louis Cardinals, who had only 83 regular-season wins, face the Detroit Tigers, who were heavily favored. Despite their underwhelming regular-season performance, the Cardinals played top-notch baseball in the postseason. Their pitching staff, led by Chris Carpenter, shut down the Tigers’ powerful offense. The Cardinals won the series in five games, making it one of the biggest World Series upsets in MLB history considering their regular-season struggles.
The 2003 World Series featured the underdog Florida Marlins against the New York Yankees, who were seeking their 27th title. The Marlins, led by young stars and guided by manager Jack McKeon, won the series in six games. Josh Beckett’s shutout performance in Game 6 at Yankee Stadium sealed one of the biggest World Series upsets, marking a significant triumph for the underdog Marlins.
Zach has been a published sports writer since 2018 specializing in college football & basketball, MLB and NFL content for multiple publications.