Who has won the World Series more times: the New York Yankees or the Boston Red Sox?

No two teams in any sport worldwide have a rivalry more intense, more storied, and more fierce than the one between the New York Yankees and the Boston Red Sox. And while both teams can lay a strong claim to have fielded the best players in the history of the game at some time or another, when it comes to the World Series, the outlook is entirely one-sided.

The New York Yankees hold a significant edge over Bean Town in terms of championships, having won the World Series a record 27 times. Their dominance began in the 1920s and has continued through various eras, marked by legendary players such as Babe Ruth, Lou Gehrig, Joe DiMaggio, Mickey Mantle, and Derek Jeter.

In stark contrast, the Boston Red Sox have a paltry-by-comparison nine World Series titles. Entirely commendable, it pales in comparison to the Yankees’ total. The Red Sox won their first championship in 1903 and followed it up with a strong run of victories in the early 20th century. However, they famously endured an 86-year championship drought, often referred to as the “Curse of the Bambino,” which was attributed to the sale of Babe Ruth to the Yankees in 1919.

Their dramatic drought-breaking win in 2004 was particularly memorable as it followed a historic comeback against the Yankees in the American League Championship Series, making the triumph even sweeter for Red Sox fans.

The disparity in World Series victories between the Yankees and the Red Sox is reflective of their organizational strategies and cultures. The Yankees are known for their aggressive pursuit of talent and willingness to spend big on high-profile players, while the Red Sox, especially in recent years, have focused on a combination of player development and more, shall we say, strategic acquisitions.

Despite the historical disparity in World Series titles, the rivalry between the Yankees and Red Sox remains one of the most intense and celebrated in all of sports. Each matchup between these teams is highly anticipated, underscoring the deep-rooted competition and mutual respect that has defined their relationship for over a century.

These are the teams that have been able to lift the Commissioner’s Trophy in the World Series since 1903: