The Fate Of Yankees’ 2025 Season Hangs On Upcoming Four Series

The Fate Of Yankees’ 2025 Season Hangs On Upcoming Four Series

By Derek McAdam

September 2, 2025

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As the 2025 MLB regular season reaches its final month, the New York Yankees enter a pivotal stretch of games that may ultimately decide their post-season fate. The Yankees will begin a three-game series with the Houston Astros tonight, before returning to Yankee Stadium to play three games against the Toronto Blue Jays and Detroit Tigers before hitting the road for three games against the Boston Red Sox.

Not only are these going to be a tough stretch of games, but it will give the Yankees potentially their last opportunity to display their skills against very good teams. To end the season, the Yankees have three games each against the Minnesota Twins and Chicago White Sox, with seven against the Baltimore Orioles. It’s not to say these will be easy games, but they won’t be as tough as this upcoming two week stretch.

But I am extremely worried about the upcoming stretch of games not only because this season has taught me that the Yankees don’t play well against better teams, but even the last two games against the White Sox could be a preview as to what may be coming.

The White Sox had two of their better starters take the mound Saturday and Sunday, and both of them had very nice starts. Unfortunately for the White Sox, their bullpen had been taxed in the first two games and could not pull away with a victory on Saturday, but managed to avoid the four-game sweep with a victory on Sunday.

Last time the Yankees played the Astros, Houston took two games of a three-game series and allowed only nine Yankee runs to cross the plate during that series. The Astros are also sending three good pitchers to the mound this series, one of whom absolutely shut the Yankees down his last time out. Plus, the Astros' bullpen is much better than the White Sox and has the potential to give the Yankees some issues yet again.

And it doesn’t stop there. The Yankees still have to face good pitching from the Blue Jays, Tigers and Red Sox, all of which have given New York trouble this season. While the Yankees are in a good Wild Card position, that status can change in just a matter of days, in this instance two weeks.

Luckily, the Yankees took care of business where they needed to. They swept the Washington Nationals at home and took three out of four on the road against the White Sox. Overall, that’s a very good week to have, even if it ended on a low note with a loss. Going forward, those wins against the Nationals and White Sox are behind them. They put up a lot of offense in that time because both teams have weaker pitching staffs and a lot of younger, less experienced players.

In the weeks ahead, the Yankees will be facing much deeper lineups with solid pitching staffs. And not only that, but this is a potential preview of what could happen to them in the playoffs. Sure, the Yankees have a nice rotation and a bullpen that seems to be figuring itself out, but their offense has fallen flat many times against the better teams. It has been my biggest concern about this team since the beginning of the season and even after winning seven games in a row, it is still a concern of mine that they won’t be able to figure out the tougher starters in the league.

The one positive that the Yankees can take away from this is that their starters are in much better form. Max Fried has turned himself around in his past couple of starts and Cam Schlittler looks much better compared to his first couple of MLB starts. Will Warren has fallen off in his past couple of starts and Luis Gil looks as if he is still trying to work on some pitches, but the Yankees don’t need them to be perfect, although that wouldn’t be a bad thing.

Going into these games, I think the games will come down to whether or not the Yankee pitching staff can limit the damage. The Yankees have not proven many times this year that they can hit good pitchers and they may need more luck than they think in the next two weeks if they even want to go 6-6 during this span.

However, it is best to take it one game at a time. The Yankees will be sending out Fried to the mound tonight and will be facing Framber Valdez, who had a rough start in the Bronx just a few weeks ago. Maybe the Yankees can take some vital points away from Valdez’s bad start at Yankee Stadium and exploit them in Houston.

Whatever happens, it is going to be a very interesting couple of weeks for the Yankees’ organization. Fans may be getting an early glimpse of what may positively or negatively happen in the playoffs, if they even make it there. But one thing is for certain: if the Yankees want to win games, they are going to have to play much different than they have in the past against these teams.

These games are going to have the atmosphere of playoff games a month before the playoffs even begin. Even if they aren’t technically playoff games, the Yankees should treat them as if they are. I don’t want to hear from Aaron Boone that the Yankees’ best baseball is still ahead. No, how about proving now that the Yankees can have a potential for “playing" better baseball next month. After all, the Yankees have not guaranteed a playoff spot, so it may not even happen.

Buckle up, Yankee fans. It’s going to be one tough stretch of baseball ahead.