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Inside The Red Sox

Why Red Sox-Yankees Series Finale Comes With Massive Stakes

More riding on this than any August game in recent memory...
Aug 29, 2026; Bronx, New York, USA;  New York Yankees first baseman Luis Garcia Jr. (26) drives in a run on a fielder's choice base hit during the third inning against the Boston Red Sox at Yankee Stadium.  Mandatory Credit: John Jones-Imagn Images
Aug 29, 2026; Bronx, New York, USA; New York Yankees first baseman Luis Garcia Jr. (26) drives in a run on a fielder's choice base hit during the third inning against the Boston Red Sox at Yankee Stadium. Mandatory Credit: John Jones-Imagn Images | IMAGN IMAGES via Reuters Connect

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We don't often talk about a "must-win" game in Major League Baseball before August ends, but Sunday is an obvious exception.

As the Boston Red Sox prepare for the last of a four-game set with the New York Yankees, they have to know this is a day to empty the tank. After dropping two of the first three, they've put themselves in a spot where one game decides far, far more than who wins the weekend.

Drama is at an all-time high, so before first pitch at 1:35 p.m. ET from the Bronx, let's break down all the stakes involved in the last regular-season game the Red Sox and Yankees will play against each other until (maybe) 2027.

What Sunday's game means for playoffs, more

Rutschman, Moran
Aug 29, 2026; Bronx, New York, USA; Boston Red Sox catcher Adley Rutschman (31) and relief pitcher Jovani Moran (47) shakes hands after winning against the New York Yankees at Yankee Stadium. Mandatory Credit: John Jones-Imagn Images | IMAGN IMAGES via Reuters Connect

Unless there's an epic collapse, and we're talking about something truly preposterous, both the Yankees and Red Sox will make the playoffs. And the odds are at least 50%, perhaps a good bit higher, that the two will face each other in a best-of-three Wild Card Series for the second year in a row to determine whose October run will be cut painfully short.

That creates the main drama at hand for Sunday, because whichever team wins this game will also take the season series, which is currently knotted at 6-6. So if the two teams were to finish the regular season with the same record, the winner of Sunday's game would be the team to host that best-of-three playoff set in front of their rabid fan base.

Boston found out just how much that matters last season, when it traveled to New York and took Game 1, then slowly shrunk away from the pressure for two nights until the offense was completely silent for the Game 3 finale against budding supervillain Cam Schlittler.

As of Sunday morning, the Red Sox trailed the Yankees by three games for the top wild-card spot. Sunday's game is essentially a three-game swing in the wild-card race, as Boston will either end the day two games back with the tiebreaker or four games back without it.

For the first time all series, one would have to give the Red Sox the edge on paper in the starting pitching matchup. All-Star lefty Ranger Suárez toes the slab for Boston, while the Yankees are countering with Will Warren, who is 1-3 with a 9.00 ERA in four starts and 20 innings against the Sox in his career.

The stakes don't get any bigger, and Boston will also presumably have Roman Anthony and/or Trevor Story in the starting lineup for the first time in over three months to add to the intrigue.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@moreviewsmedia.com