With the MLB postseason in full swing, fans can’t help but dream about the most iconic matchups that could potentially unfold. Among them, a showdown between the Los Angeles Dodgers and the New York Yankees stands out as a possibility for the 2024 World Series. These two legendary teams have a storied rivalry that has captivated baseball enthusiasts for decades, and a modern rematch could add yet another thrilling chapter to their shared history. As we anticipate the excitement of this year’s Fall Classic, it feels like the perfect time to look back at some of the greatest World Series matchups in baseball history—the kind of showdowns that made fans cheer, cry, and remember exactly where they were when it all happened.
1. 1975: Cincinnati Reds vs. Boston Red Sox
Winner: Cincinnati Reds (Series: 4-3)
Often considered one of the greatest World Series of all time, the 1975 matchup between the Cincinnati Reds and Boston Red Sox had it all—drama, talent, and unforgettable moments. The series went to a thrilling seven games, with Carlton Fisk’s iconic walk-off home run in Game 6 becoming one of the most enduring moments in baseball history. The Reds ultimately prevailed in Game 7, solidifying the “Big Red Machine” as a dynasty.
2. 2001: Arizona Diamondbacks vs. New York Yankees
Winner: Arizona Diamondbacks (Series: 4-3)
The 2001 World Series was memorable not just for its on-field action but for the context in which it was played. Following the tragic events of September 11, baseball provided a sense of unity and hope for Americans. The matchup between the Yankees and Diamondbacks was an emotional rollercoaster, culminating in a dramatic Game 7 where Luis Gonzalez’s walk-off bloop single against the legendary closer Mariano Rivera clinched the series for Arizona.
3. 1986: New York Mets vs. Boston Red Sox
Winner: New York Mets (Series: 4-3)
The 1986 World Series is perhaps best remembered for the incredible drama of Game 6, when the Boston Red Sox were just one strike away from ending the “Curse of the Bambino.” A ground ball off the bat of Mookie Wilson went through the legs of first baseman Bill Buckner, allowing the Mets to complete a miraculous comeback and ultimately take the series in Game 7. The tension and heartbreak of this series have made it one of the most unforgettable in baseball history.
4. 1956: New York Yankees vs. Brooklyn Dodgers
Winner: New York Yankees (Series: 4-3)
The 1956 World Series featured one of the most famous moments in baseball history—Don Larsen’s perfect game in Game 5, which remains the only perfect game in World Series history. This matchup was another chapter in the fierce rivalry between the Yankees and the Brooklyn Dodgers, and the Yankees eventually triumphed in seven games. The tension, history, and sheer talent on display make this series an enduring classic.
5. 1991: Minnesota Twins vs. Atlanta Braves
Winner: Minnesota Twins (Series: 4-3)
The 1991 World Series is often referred to as one of the most exciting ever played, with five of the seven games being decided by a single run. Game 7, in particular, became the stuff of legend—a 10-inning duel between Jack Morris of the Twins and John Smoltz of the Braves. Morris’s 10 shutout innings led the Twins to a 1-0 victory, capturing their second title in four years and leaving baseball fans in awe of the pitching brilliance on display.
6. 1960: Pittsburgh Pirates vs. New York Yankees
Winner: Pittsburgh Pirates (Series: 4-3)
The 1960 World Series between the Pittsburgh Pirates and New York Yankees is famous for its unexpected and thrilling ending. Bill Mazeroski hit a walk-off home run in Game 7 to give the Pirates their first title in 35 years, marking the first time in history that the World Series ended on a home run. The Yankees had outscored the Pirates significantly in the series, but Mazeroski’s iconic homer turned the tide in Pittsburgh’s favor, creating a moment that remains etched in baseball lore.
7. 2016: Chicago Cubs vs. Cleveland Indians
Winner: Chicago Cubs (Series: 4-3)
The 2016 World Series was all about breaking curses. The Chicago Cubs, who hadn’t won a championship in 108 years, faced the Cleveland Indians, themselves looking to end a title drought dating back to 1948. The series went to seven games, with the Cubs ultimately overcoming a 3-1 deficit to claim the title in an extra-inning thriller in Game 7. It was an emotional, historic, and unforgettable triumph that brought generations of Cubs fans to tears.
8. 2019: Washington Nationals vs. Houston Astros
Winner: Washington Nationals (Series: 4-3)
The 2019 World Series was notable for its unpredictability and the fact that no team won a home game throughout the seven-game series. The Washington Nationals, who were making their first-ever World Series appearance, pulled off a dramatic upset over the favored Houston Astros. The Nationals won Game 7 on the road, fueled by clutch performances from players like Stephen Strasburg and Anthony Rendon, capturing the hearts of baseball fans with their underdog story.
9. 1979: Pittsburgh Pirates vs. Baltimore Orioles
Winner: Pittsburgh Pirates (Series: 4-3)
The 1979 World Series was defined by the resilience of the Pittsburgh Pirates, who overcame a 3-1 deficit to defeat the Baltimore Orioles in seven games. Led by Willie Stargell, who was named the series MVP, the “We Are Family” Pirates showed determination and heart, rallying back and ultimately winning Game 7. Stargell’s leadership and clutch hitting became the defining story of the series, making it one of the most inspiring comebacks in World Series history.
10. 1997: Florida Marlins vs. Cleveland Indians
Winner: Florida Marlins (Series: 4-3)
The 1997 World Series was a thrilling battle between the Florida Marlins and Cleveland Indians that went the full seven games. In just their fifth season of existence, the Marlins shocked the baseball world by winning the championship. The series ended in dramatic fashion, with Edgar Renteria’s walk-off single in the bottom of the 11th inning of Game 7 giving the Marlins the victory. It was an unforgettable moment that capped off an improbable run for the young franchise.
As we dream about potential future matchups—like the possibility of a Dodgers-Yankees showdown this year—it’s clear that the World Series has produced countless legendary moments that have defined the game of baseball. Each of these iconic matchups serves as a reminder of why we love October baseball: the drama, the emotion, and the history that is written, year after year.
