How many times have the Yankees and Red Sox played each other in the postseason?
They have faced each other five times in the postseason, with the Yankees winning in 1999 and 2003, and the Red Sox winning in 2004, 2018, and 2021.
Sports / MLB
The New York Yankees and Boston Red Sox, two of the most storied franchises in Major League Baseball, continue their rivalry in the 2025 season. This series at Yankee Stadium from June 6-8 marks the first meeting of the year between these A...
The Yankees and Red Sox have followed different paths in recent years. While the Red Sox have won four championships since 2004 compared to the Yankees' one, in 2025, the Yankees are strong contenders, while the Red Sox are struggling to reach .500. The Yankees' success is attributed to a blend of high payroll and a productive farm system, demonstrating stability with Brian Cashman as general manager since 1998. The Red Sox, after a period of success fueled by changes, are now trying to find sustained success through roster building.
Historically, the rivalry is filled with memorable moments. The 2004 ALCS, where the Red Sox overcame a 3-0 deficit, stands out as a turning point. Similarly, Bucky Dent's home run in the 1978 tiebreaker game remains a painful memory for Red Sox fans. Many players, including Babe Ruth, have played for both teams, adding to the rivalry's complexity.
They have faced each other five times in the postseason, with the Yankees winning in 1999 and 2003, and the Red Sox winning in 2004, 2018, and 2021.
Babe Ruth, Roger Clemens, Wade Boggs and Johnny Damon are among the 251 players who have played for both franchises.
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