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BOSTON, MASSACHUSETTS - JUNE 03: Starting pitcher Payton Tolle #70 of the Boston Red Sox throws in the first inning against the Baltimore Orioles at Fenway Park on June 03, 2026 in Boston, Massachusetts. (Photo by Jaiden Tripi/Getty Images)

After dropping two out of three games to the Colorado Rockies, the Boston Red Sox have a difficult turnaround. Just over 24 hours after another frustrating loss in Denver, 8-6, on Wednesday afternoon, June 24, Boston returns home to open a four-game homestand against the New York Yankees.

So far this season, Boston is just 1-4 against their heated rivals. They were swept at Fenway by New York in April. After the Rockies series, the Red Sox have an American League low of 32 wins. Not what many envisioned entering the 2026 season.

After splitting their six-game road trip against the Seattle Mariners and Colorado, returning to Fenway Park to open a seven-game homestand, the pitching matchups have been announced for the next four days. It begins with a tough matchup against the Yankees’ young ace.

Boston Red Sox Reveal Pitching Matchup for New York Yankees Series

As bad as things have been this season so far for Boston, you never know what to expect against the Yankees. New York will send Cam Schlittler to the mound for the opener. He is 2-0 so far in his career against the Red Sox. In three regular-season appearances, he has a 0.83 ERA with 22 strikeouts, according to StatMuse. He’ll oppose Connelly Early in a rematch of last fall’s Game 3 AL wild-card game win by New York.

Here are the full probable matchups for this weekend in Boston,

• Thursday: Cam Sclittler (8-3, 1.71 ERA) vs. Connelly Early (6-5, 3.64 ERA)
• Friday: Will Warren (7-2, 3.45 ERA) vs. Payton Tolle (3-5, 3.08 ERA)
• Saturday: Gerrit Cole (2-2, 3.62 ERA) vs. Jake Bennett (1-3, 3.71 ERA)
• Sunday: Carlos Rodon (4-2, 3.70 ERA) vs. Sonny Gray (9-1, 2.95 ERA)

These are matchups on paper that don’t favor the Red Sox. However, it’s the Red Sox vs. the Yankees; throw the records and numbers out the window.

According to StatMuse, Cole has struggled against Boston in his career. He has a 5.42 ERA in 21 career starts. If there is a silver lining for Cole, it’s that Rafael Devers is now in Northern California with the San Francisco Giants. Devers owned Cole during his time with the Red Sox.

As far as the Red Sox are concerned, Early and Tolle are coming off strong outings against the Mariners. Bennett was good against the Rockies on Monday night and deserved a win. Gray is going up against his former team and could raise his trade value with a solid outing against the AL’s top team.

Boston Red Sox Facing Daunting Task Against the New York Yankees

Talk about two teams going in opposite directions. Boston is coming off a disappointing series in Colorado. New York is coming in off of winning two out of three games over the Detroit Tigers. They beat Casey Mize and Tarik Skubal in the final two games.

New York is 48-31 entering the series, and Boston is just 32-46. Things are spiraling downward quickly with the Red Sox. After firing Alex Cora, things haven’t gone as hoped under Chad Tracy, which puts more pressure on Chief Baseball Officer Craig Breslow.

Winning a series over the Yankees could be a step in the right direction, but all signs are pointing to Boston still becoming a big seller at the trade deadline. Two teams heading in opposite directions.