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Greatest World Series Upsets of All-Time

The World Series is the pinnacle of baseball, and it is always full of excitement and drama. But sometimes, the unexpected happens.
Published on October 19, 2023

The World Series is the pinnacle of baseball, and it is always full of excitement and drama. But sometimes, the unexpected happens. Teams that are not expected to win manage to upset the favorites and claim the championship. These upsets are some of the most memorable moments in baseball history, providing a reminder that anything is possible.

World Series Upsets

  • 1906 Chicago White Sox (93-58, .616)
    The Cubs had a regular season record of 116-36 (0.763) and experts regard them as the greatest team ever. Despite this, the “Hitless Wonders” defeated the Cubs four games to two. While hitting just .198 as a team, the White Sox held the powerful Cubs to an even more measly .196. The greatest upset in the game’s history.
  • 1974 Oakland Athletics (90-72, .556)
    The Los Angeles Dodgers (102-60, .630) led the National League in team ERA and runs scored. Despite internal conflicts that included Rollie Fingers and Blue Moon Odom getting into a fistfight, the A’s won their third straight World Series, in five games.
  • 1990 Cincinnati Reds (91-71, .562)
    Despite being the “wire-to-wire” champions of the National League, the Reds were heavy underdogs to the defending World Series champion Oakland A’s (103-59, .636). The A’s featured the Bash Brothers (Mark McGwire and Jose Canseco), a solid pitching staff, and reliever Dennis Eckersley. This was the third consecutive Series appearance for the A’s. Still, the Reds quashed their dream of a dynasty, specifically the “Nasty Boys” bullpen led by Norm Charlton, Randy Myers, and Rob Dibble.
  • 2006 St. Louis Cardinals (83-78. .516)
    The Cardinals’ worst regular season record among World Series champions solidifies this as one of the biggest WS upsets. The Cardinals beat the Detroit Tigers (95-67, .586) in five games, led by Series MVP David Eckstein. Exactly.
  • 1987 Minnesota Twins (85-77, .525)
    The Twins held the record for the worst regular season winning percentage for a World Series winner (until the 2006 Cardinals broke that record). Furthermore, the Twins achieved the distinction of being the first team to reach the World Series despite being outscored in the regular season, and they found themselves outnumbered in almost every major statistical team category. Despite all this, the Twins defeated the St. Louis Cardinals in seven games.

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  • 2003 Florida Marlins (91-71, .562)
    The Marlins came into the Series as underdogs to the mighty New York Yankees (101-61, .623) but ended up winning in six games. This Series was a battle between the young and inexpensive ($54 million payroll) Marlins roster, and the veteran and expensive ($164 million) Yankees roster. Despite the gap in pay and experience and being outscored 21-17 in the Series, the Marlins prevailed on the strength of Josh Beckett’s MVP pitching.
  • 1985 Kansas City Royals (91-71, .562)
    The Royals squeaked into the World Series in 1985, winning their division by one game, then barely getting by the Blue Jays in seven games in the playoffs. No wonder their opponents, the St. Louis Cardinals (101-61, .623), were heavy favorites to win. The Royals famously benefited from one of the worst calls in WS history, when ump Don Denkinger’s blown call in the bottom of the ninth inning of Game 6 turned a St. Louis 1-0 win (and WS trophy) into a 2-1 loss. The Royals then took Game 7 by a score of 11-0.
  • 1945 Detroit Tigers (88-65, .575)
    The Tigers faced the Cubs (98-56, .636) in the last “war time” Series, and as such, many star MLB players were still serving in the military. However, the Tigers did have future Hall of Famer Hank Greenberg in the lineup, as he had been given an early discharge. Greenberg hit the only two Detroit homers in the Series, scored seven runs overall and also drove in seven. The Tigers upset the favored Cubs in seven games, thus establishing the Curse of the Billy Goat in baseball lore.
  • 1988 Los Angeles Dodgers (94-67, .584)
    The Dodgers faced off against the Oakland A’s (104-58, .642) as underdogs. L.A. would win the Series in five games, but in most people’s minds the Series was won in Game 1. That’s when an injured Kirk Gibson (in his only AB in the Series) hit the winning HR off Dennis Eckersley. The Dodgers masked an average lineup with superior starting pitching and a bullpen that led the NL with 49 saves.
  • 1969 New York Mets (100-62, 0.617)
    The “Miracle Mets” were the first expansion team to win a World Series. Although considered heavy underdogs throughout the regular season, many forget the Mets won 100 games. However, waiting in the Series were the Baltimore Orioles, a dominating, star-studded team (109-53, .673). The Orioles were equally strong on the mound and at the plate. Behind clutch hitting and strong pitching, the Mets managed to take the Series in five games, thus cementing their status in MLB history.

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