Boston Red Sox vs New York Yankees Prediction, Odds and Picks for Today, 09/30/25

The Boston Red Sox and New York Yankees add another chapter to their storied rivalry when the teams meet in an AL Wild Card Series starting Tuesday in the Bronx. The Red Sox like the way history has treated them lately against their bitter rivals, winning the past 3 head-to-head series in 2004, 2018 and 2021. The 2004 one was memorable, as the Red Sox dug out of a 3-0 series hole to come all the way back to not only win in 7 games, but also win the World Series that season. In 2021, these teams met in the Wild Card — with Boston prevailing.

Boston turns to LHP Garrett Crochet to secure Game 1, and tilt the series in its favor. It looks ominous for the Bronx Bombers right out of the gate, as the southpaw is 13-2 with a 2.25 ERA and 1.00 WHIP across 116.0 innings in 18 road starts. He was also 3-0 with a 3.29 ERA across 27.1 innings in 4 starts against the Yankees in 2025. But this is also his first-ever postseason start. He previously made 4 relief appearances across 3.0 innings for the Chicago White Sox in 2020 and 2021, but he wasn’t a starter. LHP Max Fried was 19-5 with a 2.86 ERA and 1.10 WHIP this season, and he was 6-0 with a 1.55 ERA and 1.04 WHIP in his final 7 outings. He is 2-5 with a 5.10 ERA across 67.0 innings in 12 starts and 8 postseason relief appearances, however. This is also his first Yankees’ playoff start, so the pressure will be ratcheted to new heights. Let’s back Crochet in a low-scoring affair.

Red Sox vs Yankees prediction: Boston ML (+115) available at time of publishing. Playable to +100.

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