The Yankees and Red Sox rivalry is widely recognized as one of the most prominent in sports, with a history spanning over 100 years. Despite their frequent regular-season matchups, the two teams have only met five times in the postseason prior to this week’s meeting at Yankee Stadium during the 2025 AL Wild Card Series.
Their first playoff encounter occurred in the 1999 American League Championship Series (ALCS). After both teams advanced from their respective Division Series, the Yankees took an early lead in the series and ultimately won four games to one. The Red Sox managed a single victory behind Pedro Martinez but could not stop New York from advancing to and winning the World Series.
In 2003, another ALCS matchup saw both clubs push each other to seven games. Boston started strong but lost momentum as New York forced extra innings in Game 7. Aaron Boone hit a walk-off home run off Tim Wakefield’s first pitch in the 11th inning, sending the Yankees to the World Series.
The following year marked a historic reversal when Boston overcame a three-game deficit against New York in the ALCS—becoming Major League Baseball’s first team to win a series after trailing 0-3. David Ortiz played a pivotal role with consecutive walk-off hits, while Curt Schilling delivered seven strong innings despite injury in Game 6. The Red Sox went on to sweep St. Louis for their first championship since 1918.
After more than a decade without facing each other in October, they met again during the 2018 American League Division Series (ALDS). Both teams had surpassed 100 wins that season and entered with new managers and high-profile roster additions. Boston controlled much of the series, including a decisive victory at Yankee Stadium featuring Brock Holt’s cycle—the first ever recorded in postseason play—and advanced to claim another World Series title.
Their most recent playoff meeting before this week came during the 2021 AL Wild Card Game at Fenway Park under what would be its final year as a single-elimination format before switching to best-of-three rounds starting in 2022. Both teams finished with identical records, but Boston hosted by virtue of its head-to-head advantage. Key defensive plays involving Fenway Park’s Green Monster helped keep New York from rallying, resulting in a Red Sox victory and eventual trip to that year’s American League Championship Series.
Additionally, many fans recall their dramatic tiebreaker game for the American League East title on October 2, 1978—commonly referred to as “the Bucky Dent game.” After overcoming a large midseason deficit against Boston, New York forced and won this winner-take-all contest with Dent hitting a crucial three-run homer at Fenway Park.
As these two franchises prepare for yet another postseason showdown at Yankee Stadium this week, past meetings highlight how tightly contested and memorable their rivalry has been across generations.
