The New York Yankees and Boston Red Sox meet for the seventh time in MLB postseason history as they open a best-of-three American League Wild Card series at Yankee Stadium on Tuesday, September 29, 2026. According to historical MLB records, the two AL East rivals have split their first six postseason matchups.
The 1999 and 2003 ALCS Drama
The postseason rivalry between New York and Boston intensified with the expansion of the wild-card format. In the 1999 American League Championship Series, the Yankees defeated the Red Sox 4–1, with Boston’s lone win coming in a 13–1 victory featuring Pedro Martínez against Roger Clemens. Four years later, the 2003 ALCS delivered a seven-game thriller capped by Aaron Boone’s eleventh-inning walk-off home run off knuckleballer Tim Wakefield in Game 7 following a dramatic eighth-inning comeback against Martínez.
Boston’s Historic 2004 Comeback
Boston exacted historic revenge in the 2004 ALCS by overcoming a 3–0 series deficit against New York—the first time a Major League Baseball team accomplished the feat.
Reviving the October Rivalry in 2018
The rivalry returned to October in 2018 when a 108-win Boston squad defeated a 100-win New York team 4–1 in the AL Division Series, a matchup highlighted by Brock Holt hitting the first postseason cycle in MLB history.
Fenway Park and the 2021 Elimination
Three years later, in a single-elimination 2021 AL Wild Card game at Fenway Park, the Red Sox eliminated the Yankees 6–2 behind home runs from Xander Bogaerts and Kyle Schwarber off Gerrit Cole, alongside 5.1 innings of relief from Nathan Eovaldi.
Schlitter’s 2025 Masterclass
Most recently, the 2025 Wild Card series required a decisive third game won by the Yankees 2–1. That Game 3 featured a historic performance by rookie Cam Schlitter, who threw eight scoreless innings with 12 strikeouts and zero walks, establishing a postseason benchmark before finishing as a top AL Cy Young contender.
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