Red Sox vs. Yankees Wild Card Series Locked In; Here’s The Playoff History

It’s happening again! The New York Yankees and Boston Red Sox will face off in the 2026 MLB Wild Card Series for a second consecutive year, as Boston’s Friday afternoon victory over the Chicago Cubs secured its spot as the No. 2 American League wild-card seed; New York secured the No. 1 AL wild-card seed earlier in the week. Game 1 of the three-game set will come on Sept. 27, as the series takes place at Yankee Stadium, like last year when New York defeated Boston in three games. Here’s how the two AL East rivals fared against each other this season and their historic postseason history: The Yankees won seven of their 13 games against the Red Sox this season, with New York going 4-2 at home and 3-4 on the road. New York entered Sept. 25 at 92-67, with Boston entering the day at 85-74. The two teams first met in the playoffs in the 1999 AL Championship Series, with the Yankees handling the Red Sox in five games and going on to win the World Series in what was the first season superstar right-hander and then-five-time Cy Young Award winner Roger Clemens, who spent the first 13 seasons of his MLB career with the Red Sox (1984-96), was with the team. Their next postseason meeting came in 2003 in a dramatic showdown that went the distance. A series that included benches clearing in Game 3 and competitive games on the whole ended with a walk-off home run from Yankees third baseman — and now manager — Aaron Boone — to lead off the bottom of the 11th inning of Game 7 in a game where New York trailed 4-0 in the fifth inning. The two teams ran it back the following year (2004), but it had a much different outcome. After going down 3-0 in the series and giving up 19 runs on their home field in Game 3, the Red Sox became the first team in professional sports to win a series after trailing 3-0. Boston then went on to win the World Series for the first time since 1918. The Red Sox and Yankees wouldn’t find each other in October again until 2018, with Boston defeating New York 3-1 in the AL Division Series and going on to win the World Series for the fourth time in the 21st century (the Red Sox won the World Series in 2004, 2008, 2013 and 2018). Three years later, Boston made it three consecutive playoff series wins over New York, defeating the Yankees in the 2021 AL Wild Card Game, 6-2. Last year, the Yankees evened the score with the Red Sox at three series wins apiece, winning Games 2 and 3 of the 2025 Wild Card Series to advance to the ALDS.