Yankees-Red Sox Wild Card Series Preview: Another Chapter In Baseball’s Greatest Rivalry

The Bronx Bombers lead the all-time regular season series, 1,249–1,037–14.

In their postseason encounters, the two storied AL East opponents are 12-12 against each other. Despite the apparent stalemate, the Red Sox have won the last three October showdowns, dating back to the infamous 2004 American League Championship Series. The “BoSox” also won the 2018 American League Division Series and the 2021 wild card game.

During this season, the Red Sox won nine of 13 against the Yankees, although the latter was able to win the final series of the regular season at Fenway Park. This is the sixth postseason battle in the baseball’s greatest rivalry, and it all comes down to a best-of-three wild card series at Yankee Stadium.

How Did The Yankees Get Here?

To say that the Bronx Bombers had a turbulent offseason and spring training would be a massive understatement. After losing out on Juan Soto in free agency, Yankees general manager Brian Cashman quickly responded with his “Plan B”, which involved a series of free-agent signings and trade acquisitions.

Cashman’s backup plan was first executed when he signed Max Fried to the largest contract ever issued to a left-handed pitcher. Immediately after, the Yankees traded for 2019 National League MVP Cody Bellinger, who returned to form as one of baseball’s best outfielders this season.

Perhaps the most pleasant surprise for Yankees Universe in 2025 is Trent Grisham, who had a career-best regular season. He captivated fans with a power surge that culminated in 34 home runs and an .812 OPS, good for 10th-best among all Major League outfielders.

To the surprise of absolutely nobody, captain Aaron Judge produced another all-time great season, and he should win MVP instead of Seattle Mariners catcher Cal Raleigh.

That’s just one fascinating factoid from Judge’s stellar 2025 season. Here are more seductive statistics.

Despite the loss of Juan Soto, who formed a historic tandem with Judge a year ago, the Yankees’ lineup was better this year compared to 2024. This season, the men in pinstripes finished first in runs, home runs, OPS, wRC+, walk rate, and WAR. Much of that can be attributed to their historic barrage of round-trippers.

At the trade deadline, the Yankees acquired Ryan McMahon, David Bednar, Camilo Doval, Jake Bird, Austin Slater, and Amed Rosario. The transactions were applauded, especially because of the dire need to improve a bullpen that completed the season ranked 23rd in ERA, 18th in FIP, and had 21 blown saves. Third base had been a liability for the Yankees since Gio Urshela’s fall back to earth in 2021.

Bednar has easily been the most impactful trade acquisition; he generated a 2.19 ERA, 10 saves, and 35 strikeouts in 24.2 innings of work with the Yankees.

How Do The Yanks Stack Up Against Boston?

Despite their 4-9 showing against their arch nemesis, the Bronx Bombers match up better against the Red Sox than what their record against them would indicate.

It is true that the Red Sox have a clear advantage at third base and shortstop. But after that, the Yankees are objectively better at second base, and especially in the outfield. Judge, Bellinger, and Grisham ranked first, ninth, and tenth in OPS among all Major League outfielders.

The first base and catcher conversations are murky. Paul Goldschmidt regressed significantly in the second half; his first half OPS was .776, and his second half OPS was .631. But is Nathaniel Lowe a truly superior option? It seems about even at cornerman.

Austin Wells’ disappointing campaign was somewhat alleviated by his .892 OPS over the last 30 days of the season. Compared to Carlos Narvaez, who was traded from the Yankees to the Red Sox last December, Wells’ offensive output is about even, although Narvaez is far better defensively.

As far as designated hitter goes? This isn’t a conversation. Giancarlo Stanton has been sensational, even in limited action this season. He and Masataka Yoshida are not in the same stratosphere.

Leading the rotation for the Red Sox is ace Garret Crochet, who has often had the Yankees’ number this season. Behind him are Brayan Bello and Lucas Giolito, who both had very good seasons. The Yankees are able to counter that with Max Fried, Carlos Rodon, and likely third starter Cam Schlittler.

What could prove to be a decisive factor is the dichotomy between the bullpens. The Red Sox’s bullpen finished second in ERA and fourth in FIP, far greater than the mediocre production from the Yankees’ relievers.

End Of My Yankees-Red Sox Rant

The Yankees have not defeated the Red Sox in a playoff series since 2003, when current Yankee skipper Aaron Boone hit one of the most iconic home runs in Major League history. Since then, the Yankees are 0-3 in postseason series against their greatest rival.

Can the Yankees finally exorcise their 21st-century demons against the BoSox, or will they falter yet again? There’s only one way to find out.

As for the rest of the playoff field, here’s a look at the other ball clubs competing for the Commissioner’s Trophy.