What Was the Biggest Upset in World Series History?

The World Series is the pinnacle of professional baseball and has produced some of the most iconic moments in sports history. From dramatic walk-off home runs to clutch performances, the Fall Classic always provides fans with plenty to talk about.

However, there have been a few occasions where the outcome has shocked even the most die-hard baseball fans. In this article, we’ll take a look at what was the biggest upset in World Series history.

1919 World Series: Cincinnati Reds vs Chicago White Sox

The 1919 World Series between the Cincinnati Reds and Chicago White Sox will forever be remembered as one of the darkest moments in baseball history. The White Sox were heavily favored to win due to their dominant regular season performance and star-studded lineup featuring players such as Shoeless Joe Jackson and Eddie Cicotte.

However, it was later revealed that some members of the White Sox had conspired with gamblers to intentionally lose games in exchange for money. This scandal, now famously known as the “Black Sox Scandal,” resulted in eight players being banned from baseball for life and forever tainting the legacy of the 1919 World Series.

1954 World Series: New York Giants vs Cleveland Indians

The 1954 World Series featured two powerhouse teams – the New York Giants and Cleveland Indians. The Indians had won an incredible 111 games during the regular season and were led by future Hall of Famers such as Bob Feller and Larry Doby.

Despite their dominance, it was the underdog Giants who emerged victorious in a stunning four-game sweep. Led by pitcher Johnny Antonelli and outfielder Willie Mays, who made “The Catch” – one of the most famous plays in baseball history – during Game 1, the Giants shocked baseball fans across America with their unexpected triumph.

1969 World Series: New York Mets vs Baltimore Orioles

The 1969 World Series between the New York Mets and Baltimore Orioles is often cited as one of the greatest upsets in sports history. The Mets were a relatively new team, having only been established in 1962, and had never finished higher than ninth place in their division.

Meanwhile, the Orioles had won 109 games during the regular season and boasted an impressive lineup featuring future Hall of Famers such as Frank Robinson and Brooks Robinson. However, it was the Mets who came out on top in five games, with pitcher Tom Seaver leading the way with two dominant performances.


While there have been many surprising outcomes throughout World Series history, the 1919 Black Sox scandal will always be remembered for its impact on baseball as a whole. However, when it comes to on-field performance, the underdog victories by the 1954 Giants and 1969 Mets stand out as two of the biggest upsets of all time. No matter what happens in future World Series matchups, these moments will forever be etched in baseball history as examples of unexpected triumphs against all odds.

  • Key Takeaways:
  • The 1919 World Series was tainted by the Black Sox Scandal.
  • The 1954 Giants shocked fans with a four-game sweep over heavily favored Cleveland Indians.
  • The underdog New York Mets upset powerhouse Baltimore Orioles in five games during the 1969 World Series.