Inside The Pinstripes

Yankees Snap Two Decades Long Drought Against Red Sox

The New York Yankees were on their way to be sent home by the Boston Red Sox after game one but their 21 year drought is over.
Joseph Randazzo|
Oct 2, 2025; Bronx, New York, USA; New York Yankees players celebrates in the clubhouse after defeating the Boston Red Sox in game three of the Wildcard round of the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images
Oct 2, 2025; Bronx, New York, USA; New York Yankees players celebrates in the clubhouse after defeating the Boston Red Sox in game three of the Wildcard round of the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

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New York Yankees

Twenty-one years, 11 months, and 16 days separate the last time the New York Yankees defeated the Boston Red Sox in the postseason. Manager Aaron Boone played a big part in both.

In 2003, Boone picked up Mariano Rivera by sending Tim Wakefield's knuckleball to the left field seats. Both Charlie Steiner and John Sterling serenaded the players celebrating on the field that night, announcing in unison that the Yankees won, as a bevy of Hall of Famers and one future manager threw themselves in a pile, ecstatic for another World Series appearance.

In 2025, Boone was still on the field, but he had a decision to make. How long does he let this rookie pitcher, Cam Schlittler, go for? The answer was eight innings. For all of his criticisms, that was his gutsiest decision since being hired as skipper in 2018.

It may be hard to alleviate the disappointment of what happened in 2004, when the Yankees collapsed, blowing a 3-0 lead to their hated rival. Still, two decades of one-sided October dominance were finally upended. The Wild Card round may not have the luster of a seven-game series, but it's the format both teams were given, and anyone downplaying it is probably deceiving themselves. Especially a large group of Boston fans, led by Jared Carrabis, singing "New York, New York" after their game one win.

Bostonian confidence was not without reason, though. 21 years of using the Yankees as a stepping stone is a long time.

After 2004, it wouldn't be until 2018 that the Yankees and Red Sox would meet in October. That series was a one-sided affair, with the Yankees taking one in Boston, and Boston immediately responding by dropping 16 runs at Yankee Stadium, before sending them packing for the season the following night.

The two met again in 2021, after the pandemic. This time, there was a little more juice to the rivalry. Alex Cora had returned after his suspension, during which he had been identified as one of the masterminds of the 2017 Astros scandal. His 2018 team also had baggage, as they were caught using the replay room, and guys like Steve Pearce and Mitch Moreland went from good players to suddenly playing like all-stars after being traded over to Boston.

The Yankees didn't exact revenge in the 2021 Wild Card, and that trend of losing to Boston continued. They beat up ace Gerrit Cole, knocking him out of the game after two innings and three earned runs.

2025 was a different story. Cora had once again been pegged as a genius after allowing the potential Cy Young winner to dominate, and then followed that up by bringing in one of the most dominant closers in baseball. That would be the only game Boston got this postseason.

The Yankees staved off elimination twice, outlasting Boston in a tough game two. Game three involved a historic outing by a rookie pitcher who outclassed even Crochet from game one. The result wasn't Carrabis singing "New York, New York." It was Frank Sinatra, and the baseball universe in the Bronx was feeling grounded for the first time in a while.

Boone discussed his team's grit after taking game three.

"These guys just kept playing," Boone said, according to Gary Phillips of the Daily News. "Honestly, going into the night for me personally, it felt like as pressure-packed a game as I have ever been in, as a player, manager, going into the World Series … just because of the context in my brain of what I think our team is. A great opponent. A storied opponent. Here, down one. The boys answered the bell and played great baseball."

What Boston did in two of those three series, where they vanquished the Yankees over the course of two decades, was win the World Series. It's something the Yankees now hope to do. There's a long road ahead for them, with multiple playoff series to be won before they have a chance to hoist their 28th championship.

For now, sending home a bitter rival is a good start.

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Joseph Randazzo
JOSEPH RANDAZZO

Joe Randazzo is a reference librarian who lives on Long Island. When he’s not behind a desk offering assistance to his patrons, he writes about the Yankees for Yankees On SI. Follow him as @YankeeLibrarian on X and Instagram.

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