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Does regular season performance against rivals translate to October?

When the dust settles on the Yankees’ regular season and a likely trip to the postseason, a prevailing narrative will enter the conversation. Most likely, the Yankees will have to go through somebody in the AL East to get back to the World Series and they might have to go through both the Blue Jays and Red Sox — two teams that they have combined to go 9-16 against in 2025 (even including the past couple days of wins in Boston). The Bombers have played some of their worst baseball, both fundamentally and results-wise, against the two teams they’re fighting with for positioning.

This is a concerning fact. The Red Sox have all-too-often had the Yankees’ number, especially with the likes of Garrett Crochet and Brayan Bello in their rotation. The Blue Jays went 6-1 against the Yanks at the Rogers Centre, a place where the Yankees made 11 errors in just seven games in some of their sloppiest games of the season. For most fans, there’s no optimism in these potential matchups come October, especially as the Yankees and Red Sox are currently lined up to face off in the Wild Card Series with the top-seeded Blue Jays awaiting the winner in the ALDS if the season ended today.

But, how much of this really matters? Sure, it’s the same personnel and these matchups have a playoff feel, but how translatable is it to October? The answer: partially, but not completely

In the last 20 seasons, the Yankees have been eliminated from the playoffs 14 different times. Of the 14 opponents to eliminate them, the Yankees went 3-10-1 in the season series against those teams, including eight straight losses (and on the other side of the coin, losing to Cleveland in the 2007 ALDS despite going a perfect 6-0 against ’em in the regular season). While not encouraging at all, it’s important to note that only a few of the 10 losses were as dominant season series victories as the Blue Jays and Red Sox have had against the Yankees this season, with several—including 2018 and 2021 against Boston—being decided by just one game.

One example is the 2021 season. While the Red Sox narrowly won the season series, the Yankees dominated baseball’s oldest rivalry in the second half, going 9-3 against Boston starting on July 17th. The momentum was completely in the Bombers’ favor, with the good guys winning each of the last six games of that season series, including sweeps at Yankee Stadium in August and a memorable sweep in Fenway that nearly knocked Boston out of the playoffs entirely. If the Yankees can pull off the sweep at Fenway Park tonight, it might have an eerily similar feel.

Unfortunately, we all know the story from there. The one-game difference in the season series saw Boston host the Wild Card Game and Gerrit Cole’s first Yankee playoff start with fans in attendance blowing up in smoke. While we now know of the Yankees’ ace’s longtime struggles against the Sox, at the time, it wasn’t much (and he was battling a bum hamstring to boot). He had a 4.03 ERA as a Yankee against Boston entering that game, which isn’t Cole-like but not horrible. Since that game? A ghastly 7.32. This current team hasn’t been able to hit Bello or Crochet (though yesterday was a start against Bello), but there’s no telling what happens when both make their playoff starting debuts.

Around the league, switches can flip on a dime. The Dodgers lost 8 of 13 to the Padres, and the Mets lost 7 of 13 to the Phillies. Despite this, both moved on to the NLCS. The Mets also went 1-5 in the regular season against the Brewers team they beat in the Wild Card Series. Back in 2023, the Astros went 9-4 against the Rangers in the regular season, including seven of the last eight. The Rangers would proceed to win four games at (then) Minute Maid Park en route to a pennant and a World Series. That whole Rangers team is an enigma, completely collapsing in August and September before running roughshod on the league come October — with a bullpen that was awful for much of 2023 before getting it together at just the right time.

The Braves dominated the NL East in the regular season in both 2022 and 2023, but got embarrassed by the Phillies in back-to-back NLDS despite going a combined 19-13 against them in the regular season. Even the mighty Dodgers went 14-5 against the Padres in 2022 and 8-5 against the Diamondbacks in 2023, only to turn in two terrible performances in back-to-back NLDS.

The point is, the regular season might be able to tell you how teams match up, but it isn’t the end-all-be-all. The Yankees will have finished up their season series’s against Boston and Toronto with series wins, which is good for confidence, but doesn’t say anything. Neither does what happened in July at Rogers Centre or June at the start of the summer swoon. The Yankees have all the tools they need to make a deep October run, and how they’ve performed against teams in the regular season won’t be the reason they sink or swim.