The New York Yankees have 10,684 wins through the 2023 season, making them the team with the most wins in American League history. The Boston Red Sox are second, with 9874 wins.

(You might also be intersted in our look at the team with the most wins in National League history.)

Throughout nearly their entire history, these two storied franchises have been bitter rivals, engendering generations of diehard fans on both sides of the aisle.

The Yankees began American League play as the New York Highlanders in 1903, adopting the nickname “Yankees” in 1913. Nearly seven years later, in December of 1919, the Yanks bought Babe Ruth from the Red Sox, a deal that would change the course of baseball history.

Meanwhile, the Red Sox began A.L. life as the Boston Americans in 1901, becoming the Red Sox in 1908. They won five World Series between 1903 and 1918, the year before they sold Ruth to their rivals. Infamously, they wouldn’t win again until 2004 as the so-called “Curse of the Bambino” led them to the brink of glory only to dash their dreams again and again … and again.

Overall, the Yankees have won 40 American League pennants and 27 World Series championships, while the Sawx have claimed 14 American League flags and 9 world titles.

Besides the Sultan of Swat, other notable men who have played for both the Yankees and Red Sox include (amont others):

  • Rickey Henderson
  • Elston Howard
  • Wade Boggs
  • Johnny Damon
  • Ben Chapman
  • Mike Stanley
  • Don Baylor
  • Jacoby Ellsbury
  • Everett Scott
  • George Scott