Red Sox Dominate Yankees In 2025, Until It Matters Most… September

By: Chris Felico

The Boston Red Sox managed to avoid a sweep at Fenway Park on Sunday, salvaging the final game of their three-game set against the New York Yankees. But even with that 6-4 win, the bigger story is how the Yankees stormed into Boston and took two of three to seize control of the first Wild Card spot while keeping their faint American League East hopes alive. For New York, it was the first series win over their rivals in 2025, finally snapping a season-long frustration after going 2-8 against Boston entering the weekend. For the Red Sox, however, the series loss created a troubling reality: they are suddenly clinging for dear life in the playoff picture, with the Astros, Mariners, and Rangers all threatening to potentially leapfrog them in the Wild Card standings.

On paper, a 9-4 season series advantage against the Yankees should be a source of confidence. But the Red Sox’s inability to deliver when it matters most has become a troubling theme. Since 2020, Boston is just 4-21 against New York in games played in September, a stretch that now includes this weekend’s gut-punch series loss. That record isn’t merely a quirk—it highlights a consistent failure in high-pressure situations. September baseball has always carried extra weight, and with MLB’s expanded playoff format keeping more teams alive deep into the season, the stakes are even higher. The Yankees have repeatedly risen in those moments, while the Red Sox have too often shrunk.

This latest series fit the pattern perfectly. In Game 1, the Red Sox were nearly no-hit, an offensive no-show that set a grim tone. In Game 2, they staged a late rally that never felt convincing, falling short in a loss that was more frustrating than inspiring. Only in Game 3, with ace Garrett Crochet on the mound, did Boston finally secure a victory—but even then, they nearly blew a 6-0 lead before hanging on 6-4. What should have been a stabilizing win instead left fans exhaling nervously, the kind of result that feels less like a statement and more like an escape.

The most alarming aspect of this series wasn’t just the losses—it was how they came. Boston rolled out its top three arms in Lucas Giolito, Brayan Bello, and Garrett Crochet, yet none looked dominant. Bello and Giolito were passable but not imposing, while Crochet nearly watched his early gem unravel late, in which he gave up 3 earned runs and 3 home runs. Against a Yankees team that had just one of its top pitchers, Max Fried, on the mound this weekend, the Red Sox had every reason to feel confident. Instead, New York flipped the script, beating their rival in their own ballpark while facing Boston’s best. That’s the kind of outcome that lingers in both dugouts—the Yankees walking taller, the Red Sox looking shaken.

Now, with just a couple of weeks left in the regular season, the Red Sox find themselves in a dangerous position. What once looked like a promising campaign risks unraveling into a fourth straight year without October baseball. The Yankees, meanwhile, are surging at the right time, controlling the Wild Card race and eyeing a late push for the division. It doesn’t hurt that the Yankees have the easiest remaining schedule of all teams that are in a playoff position currently, while the Red Sox have the toughest in the American League, History has already shown that when September arrives, New York thrives and Boston falters—and unless the Red Sox can buck that trend immediately, the 2025 season could end the same way too many recent ones have: watching the playoffs from home.