A couple of days ago, I read an article about the World Series odds. Well, I’m not going to predict which team is going to win the 2026 Fall Classic. But after reading the article, I was just wondering about a thing among the teams that won the World Series this century.
Winning a World Series title isn’t easy. In particular, a team hasn’t even played in the World Series. Nonetheless, in this century, there are some teams that actually won multiple World Series titles. Among those teams, are they really good at playing in the Fall Classic?
Well, let’s not look at the calendar too strictly. Let’s check the World Series winners from 2000 to 2025. Hence, there are 6 teams that won multiple World Series titles from 2000 to 2025.
Firstly, the Yankees, the Astros and the Cardinals each won 2 World Series titles from 2000 to 2025. The Yankees actually have made 5 World Series appearances from 2000 to 2025. They won the title in 2000 and 2009. Nonetheless, they lost in 2001, 2003 and 2024. In those 5 World Series appearances, the Yankees played 29 games and won 14 times. Hence, their winning percentage in the Fall Classic from 2000 to 2025 was below .500. The Astros also have made 5 World Series appearances from 2000 to 2025. They won the title in 2017 and 2022. But they lost in 2005, 2019 and 2021. In those 5 World Series appearances, the Astros played 30 games and won 13 of them. Therefore, the Astros don’t have a winning percentage of .500 in the World Series this century. Moreover, the Cardinals have made 4 World Series appearances this century. They won 2 times. The first one was in 2006 and the other one was in 2011. Nonetheless, they lost in the Fall Classic in 2004 and in 2013. In total, they played 22 games in those 4 World Series and they won 10 games. Thus, their winning percentage is below .500 as well.
In addition, the Giants have made 4 appearances in the Fall Classic this century. They lost in the 2002 World Series. Nonetheless, they had an “even-year” dynasty in the early 2010s. They won the Fall Classic in 2010, 2012 and 2014. In total, they played 23 games in the World Series this century and won 15 games. Their winning percentage in the World Series is over .600 this century.
Furthermore, the Dodgers won the World Series title in 2020, 2024 and 2025. Nonetheless, they lost in 2017 and 2018. This century, the Dodgers have played 30 games in the World Series. They won 16 of them and have a winning percentage over .500.
Finally, the Boston Red Sox not only ended the curse of bambino but also won the World Series 4 times this century. The Red Sox actually have played very well in the World Series this century. They won 16 times in 19 games. Yes, the Red Sox only lost 3 games in the Fall Classic this century. They have a winning percentage over .800 in the Fall Classic this century.
Looking at the teams that won multiple World Series titles, the Red Sox actually are the only team that didn’t lose a series and their winning percentage is .842, which is incredible. Meanwhile, the Dodgers and the Giants each won 3 titles and their winning percentage is over .500 in the Fall Classic this century.
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