Red Sox-Yankees History Is On Boston's Side For Wild Card Round

The Boston Red Sox will face the New York Yankees...

Aug 14, 2023; Atlanta, Georgia, USA; A detailed view of a New York Yankees hat and glove on the bench against the Atlanta Braves in the third inning at Truist Park. Mandatory Credit: Brett Davis-Imagn Images | Brett Davis-Imagn Images

The Boston Red Sox and New York Yankees are going to write another chapter in their longstanding rivalry beginning on Tuesday night at Yankee Stadium.

After a roller coaster of an end to the season, the Red Sox got into the playoffs with the No. 2 American League Wild Card spot. The Yanekes secured the top American League Wild Card spot despite a late push for the top spot in the American League East.

Now, these two will duke it out in a three-game series for a chance to advance to the American League Division Series and take on the Blue Jays.

The Boston Red Sox will face off against the New York Yankees

Apr 7, 2025; Detroit, Michigan, USA; New York Yankees baseball hats and gloves in the dugout out in the eighth inning against the Detroit Tigers at Comerica Park. Mandatory Credit: David Reginek-Imagn Images | David Reginek-Imagn Images

If you have been a Red Sox fan for a while, you likely know the whole Red Sox-Yankees star. The "Curse of the Bambino." The Yankees winning World Series after World Series while the Red Sox struggled. Boston coming close to taking down its biggest rival in 2003, but having its hard broken again. And then, finally getting over the hump with arguably the greatest comeback in professional sports history -- or at least just baseball -- as the Red Sox stormed back after being down three games against New York to advance to and win the World Series in 2004.

Since then, the rivalry actually has been all Boston from a playoff perspective. Tim Healey of the Boston Globe pointed out on social media that Boston enters the Wild Card series winners of the last three playoff series between these two rivals: 2004, 2018, and 2021.

The Red Sox haven’t lost to the Yankees in the playoffs since 2003.

They beat them in 2021, 2018, and — some might remember — 2004.

— Tim Healey (@timbhealey) September 28, 2025

In 2021, the Red Sox were the No. 4 seed and the Yankees were the No. 5 seed. Boston knocked the Yankees out and advanced to take on another AL East foe in the ALDS in the Tampa Bay Rays. The Red Sox advanced to the American League Championship Series, but lost against the Houston Astros.

The Yankees have the overall success throughout the two teams' history with a plethora of World Series titles, obviously. But, recently, the Red Sox actually have had New York's number.

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