For weeks, a Red Sox-Yankees meeting in the first round of the 2026 Major League Baseball postseason has felt like the obvious outcome. It still might be. But with the regular season winding down, it’s not locked in yet.
Boston is sitting on a magic number of three to clinch the No. 2 American League Wild Card spot, with five games remaining.
The Red Sox are the clear favorite to grab that position and set up a Wild Card round against New York, but the path isn’t completely sealed. The Chicago White Sox are three games behind, while the Cleveland Guardians are technically two back - though they currently hold the top spot in the American League Central, which makes that gap a little misleading.
The wrinkle comes through Cleveland. Boston owns the tiebreaker over Chicago, but the Red Sox could still lose the tiebreaker to the Guardians.
That matters because Boston dropped Tuesday’s game to Cleveland, leaving the two clubs tied 2-2 head-to-head with two games still to be played. The Red Sox have also hit a rough patch, going 4-6 over their last 10.
That opens the door to some messy math. If Boston, Cleveland and Chicago all finish with the same record and the Red Sox lose the tiebreaker to the Guardians, Boston could slide all the way to the No.
3 Wild Card spot. Right now, Boston is 84-73, Cleveland is 82-75 and Chicago is 81-76, and all three teams have five games left.
The combinations are simple enough, even if the implications are not. If the Red Sox go 1-4, the Guardians go 3-2 and the White Sox go 4-1, all three clubs would land at 85-77. If Boston finishes 2-3, Cleveland 4-1 and Chicago 5-0, they’d all end up 86-76.
There’s another layer, too: if Cleveland takes the tiebreaker from Boston this week, then the Guardians would win that race against the Red Sox but lose it to Chicago. In that case, if all three teams finished tied, Chicago would take the AL Central, Cleveland would claim the No.
2 Wild Card spot and Boston would fall to No. 3.
Boston has already clinched a playoff berth, so the Red Sox are guaranteed at least the No. 3 Wild Card position.
Even so, the No. 2 spot can still slip away. If Boston were to lose its final five games and the White Sox won at least four of their last five, Chicago could pass them.
So the Yankees matchup is still the most likely finish. It just isn’t inevitable yet. Boston is only a few wins - or a few losses by Cleveland and Chicago - away from making it official.
In Other News...
Yankees May Be Preparing A Playoff Infield Change Fans Saw Coming
The Yankees have spent enough time looking for answers at third base that Aaron Boone is now openly floating one of the cleaner possibilities. Boone said Anthony Volpe will probably get a look there sometime this week, a move that lines up with what the organization has seen before from the shortstop and with the modest offensive uptick he has shown compared with Ryan McMahon. With home-field advantage already locked in for the AL Wild Card Series, New York has a little breathing room to test whether a postseason adjustment can sharpen the infield before October starts in earnest.
Volpe has handled third base before in Triple-A, so this would not be a blind experiment so much as a practical shuffle with real stakes attached. The bigger question is how the Yankees want their best defensive and offensive alignment to look when the games begin to count, and whether this kind of late-week change is the first sign of a more aggressive playoff setup. Boone has not finalized anything yet, but the timing makes it clear the team is at least considering a different shape on the left side of the infield. [Read more 🡒]
Yankees Just Entered An Ownership Era Fans Never Saw Coming
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For a team whose identity has long been tied to the Steinbrenner family, the bigger picture matters just as much as the price tag. The family still holds just over 60 percent of the club, keeping control in familiar hands even as outside capital becomes a bigger part of the modern baseball landscape. What this shift means for the Yankees day to day is still unfolding, but the sale alone shows how far the financial power structure around the sport has moved. [Read more 🡒]
Yankees Triple-A Era Ended With A Twist Fans Never Saw Coming
The Scranton/Wilkes-Barre RailRiders went out with a little bit of everything in their final game under that name, edging Jacksonville 6-5 in 10 innings on Sept. 19. In a fittingly strange finish for a longtime Yankees Triple-A affiliate, catcher Edinson Duran wound up taking on pitching duty and was credited with the win, giving the club one last memorable night before the name change.
The scheduled season finale the next day never got played, with rain and unplayable field conditions bringing the curtain down early on the RailRiders era. The franchise is set to rebrand for the 2027 season, which means the Yankees' top minor league stop has now closed one chapter before the next one officially begins. [Read more 🡒]