Yankees Start Red Sox Playoff Series With Major Challenge

It's official: the New York Yankees are taking on their arch-nemesis, the Boston Red Sox, in a three-game series to kick off the 2025 MLB Wild Card round. While the Pinstripes might have a stronger record than their rivals from Massachusetts, they'll start the series facing down one man that's been a problem for them all year: Red Sox ace Garrett Crochet

Crochet has been a thorn in the Yankees' side this season, with the Red Sox winning all four of his starts against the Pinstripes in 2025. Crochet, who is in his first season with Boston after spending the first four years of his career with the Chicgo White Sox, is throwing a 2.59 ERA and 1.03 ERA this season: the best numbers of his career.

Sep 8, 2025; West Sacramento, California, USA; Boston Red Sox pitcher Garrett Crochet (35) throws a pitch against the Athletics during the fourth inning at Sutter Health Park. Mandatory Credit: Ed Szczepanski-Imagn Images | Ed Szczepanski-Imagn Images

The Yankees are going to have to play perfectly to extend their eight-game win streak and keep the momentum up against the Red Sox. With Crochet on the mound and a Boston team hungry to prove themselves, New York must avoid sloppy defensive play and get runners on base, two things they've struggled with mightily in 2025. Momentum has been everything to this Yankees team, and losing it against Crochet in the first game of the series could spell disaster.

Fortunately for the Yankees, slugger and captain Aaron Judge doesn't seem phased by the impending matchup. The MVP candidate told SNY that he was excited to play Crochet once again, hopefully indicating a winning attitude that will help propel the Bronx Bombers to a victory against the pesky left hander.

“He’s a tough matchup, if not one of the best, the best pitcher in the game right now. Probably on his way to a Cy Young," Judge said. "It's impressive what he's done so far this year, and I'm looking forward to facing him."

Aaron Judge says he's looking forward to facing Garrett Crochet:

"He's a tough matchup, if not one of the best, the best pitcher in the game right now probably on his way to a Cy Young" pic.twitter.com/vKL4HKvIMz
— Yankees Videos (@snyyankees) September 28, 2025

Fellow left-hander Max Fried will take the mound for the Yankees against Crochet as both teams look to push past their rival to the division round. While Carlos Rodón is listed as the Yankees' starting pitcher for Game 2, the team has yet to make a decision about the Game 3 starter, though many suspect rookie flamethrower Cam Schlittler will get the start. Boston has not announced their starting pitchers for the final two contests.

The AL East showdown only continues into the AL Divisional Round, as the winner of the Yankees vs. Red Sox series will go on to face the Toronto Blue Jays. The Blue Jays commanded the best record in the division and the American League, earning a first round bye.

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