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By Tim Crowley
Sports and Entertainment Network
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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.
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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 Missing
While 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.
Boston will also need a new plan for a potential Game 3 after Monday's announcement that starter Lucas Giolito would not be on the roster for the series with an elbow issue.
Red Sox-Yankees Playoff History
Boston 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.
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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.
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The 2018 meeting also featured the lone meeting where both teams won 100 games during the regular season.
Series Schedule
Game 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 Pitchers
Game 1: LHP Garrett Crochet (BOS) vs. LHP Max Fried (NYY)
Game 2: RHP Brayan Bello (BOS) vs. LHP Carlos Rodon (NYY)
Game 3: RHP TBD (BOS) vs. TBD (NYY)
Matchups To Watch
Red Sox RHH vs. Yankees LHP Starters
The 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 will make infielder Romy Gonzalez and outfielder Rob Refsnyder two of the most important players in the series.
Both right-handed bats emerged as lefty killers during their careers, which continued this season. Gonzalez hit lefties to a .331 clip with seven home runs and a .978 OPS in 143 plate appearances. Refsnyder added to that run with a .302 average, seven home runs of his own and a .959 OPS in 138 plate appearances.
The Red Sox have the starting pitching to compete in this series, but the offense needs a jolt with Anthony still on the shelf. If the righties can lift Boston with swings from Gonzalez and Refsnyder, that could be enough to send the Red Sox to the ALDS.
Yankees Bullpen vs. Red Sox
New York went all out to build a lethal bullpen at the trade deadline. The Yankees acquired Camilo Doval and David Bednar to join Luke Weaver and Devin Williams. That group sounds legitimately unhittable on paper, though the production didn't match the hype over the final two months of the season.
New York's offense and rotation are capable in this series. Will the bullpen meet the moment to nail down wins?
Wild Card Format Implications
These series can be over quick, as we've learned through its previous installments in 2020 and each series since 2022.
For reference, since the three-game set became the format of the wild card round fully in 2022, the team that won Game 1 has won all 12 of the wild card series over the three-year span, as referenced by NESN's Tom Caron on X.
For either the Red Sox or Yankees to advance, Game 1 marks an all-but-likely must-win game. But aren't they all in the playoffs to some degree?
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