By Tim Crowley

Copyright newsweek

The Boston Red Sox and New York Yankees will clash in the postseason for the fifth time in the 21st century.

New York, the No. 4 seed, is set to host Boston, the No. 5 seed, in the American League Wild Card Series. The best-of-three set starts Tuesday night at Yankee Stadium. The winner of the series will advance to face another division rival in the ALDS in the Toronto Blue Jays.

Here is everything you need to know about both teams’ 2025 season, the postseason history of the Red Sox-Yankees rivalry and a handful of matchups and figures to watch in this series.

NEW YORK, NEW YORK – AUGUST 24: Trevor Story #10 of the Boston Red Sox forces out Aaron Judge #99 of the New York Yankees at second base and throws to first to complete the double play during the first inningat Yankee Stadium on August 24, 2025 in New York City. (Photo by Vincent Carchietta/Getty Images)

2025 Season Series The Red Sox took a strong advantage in the season series with a 9-4 record against the Yankees. In specific reference to the upcoming playoff setting, Boston took care of business at Yankee Stadium at a 5-2 clip. The most recent series in the Bronx came in late August when the Red Sox took the first three games of a four-game weekend set.

Stars MissingWhile both AL East rivals still have plenty of talent in this series, some big names will still miss this series.

Yankees ace Gerrit Cole missed the entire season after Tommy John surgery and won’t return until next season. For Boston, the Red Sox took a massive gut punch when star rookie Roman Anthony (.292 AVG, .859 OPS) suffered an oblique injury on Sept. 2 and missed the remainder of the regular season. Anthony is yet to resume baseball activities, so Boston would need a deep run in October to give him a chance to return in the playoffs.

Red Sox-Yankees Playoff HistoryBoston and New York have a rivalry that spans over a century, though years of different postseason formats across baseball history have only produced five previous playoff series matchups, with this year marking a sixth.

BRONX, NY – OCTOBER 16: Aaron Boone #19 of the New York Yankees hits the game winning home run in the bottom of the eleventh inning against the Boston Red Sox during game 7 of the American League Championship Series on October 16, 2003 at Yankee Stadium in the Bronx, New York. (Photo by Al Bello/Getty Images)

Here’s how the previous October duels went:1999 ALCS – Yankees win series 4-1 (New York eventually won 1999 World Series over Atlanta Braves)2003 ALCS – Yankees win series 4-3 (New York eventually lost 2003 World Series to Florida Marlins) 2004 ALCS – Red Sox win series 4-3 (Boston eventually won 2003 World Series over St. Louis Cardinals) 2018 ALDS – Red Sox win series 3-1 (Boston eventually won 2018 World Series over Los Angeles Dodgers) 2021 AL Wild Card Game – Red Sox win game 6-2 (Boston eventually lost 2021 ALCS to Houston Astros)

Boston advanced in three of the five previous meetings, including three straight dating back to 2004. The Red Sox and Yankees each hold 12 wins in the 24 total playoff games between the rivals.

These meetings have often been rather consequential in the grand scheme of that October’s MLB playoff picture. The winner of Red Sox-Yankees went to the World Series in four of these meetings and won the Fall Classic in three of them.

Classic moments emerged in this history from three pitching duel between Roger Clemens and Pedro Martinez, Aaron Boone’s walk-off home run to win the 2003 ALCS and cap off the Yankees’ Game 7 comeback as well as David Ortiz’s back-to-back walk-off hits in 2004 as the Red Sox became the first team in baseball history to erase a 3-0 series deficit to win the 2004 ALCS.

BOSTON – OCTOBER 17: David Ortiz #34 hits the game winning two-run home run against the New York Yankees in the twelfth inning during game four of the American League Championship Series on October 17, 2004 at Fenway Park in Boston, Massachusetts. (Photo by Ezra Shaw/Getty Images)

The 2018 meeting also featured the lone meeting where both teams won 100 games during the regular season.

Series ScheduleGame 1: Tuesday, Sept. 30 @ 6:08 p.m. ET (ESPN) Game 2: Wednesday, Oct. 1 @ 6:08 p.m. ET (ESPN)*Game 3: Thursday, Oct. 2 @ 6:08 p.m. ET (ESPN)

*Game 3 if necessary, time subject to change based on other series

Probable PitchersGame 1: LHP Garrett Crochet (BOS) vs. LHP Max Fried (NYY)Game 2: RHP Brayan Bello (BOS) vs. LHP Carlos Rodon (NYY)Game 3: RHP Lucas Giolito (BOS) vs. TBD (NYY)

Matchups To Watch Red Sox RHH vs. Yankees LHP StartersThe Yankees send two talented southpaws to the mound to start the series in Fried (19-5, 2.86 ERA) and Rodon (18-9, 3.09 ERA).

Red Sox manager Alex Cora often deployed a completely different lineup against left-handed pitching to best utilize his platoons and squeeze out victories. That strategy …