We have a rematch of the 2025 AL Wild Card Round between the Boston Red Sox and the New York Yankees, as these AL East rivals have been on a crash course in the postseason for a while. In 13 regular-season meetings, the Yankees had a 7-6 edge, but did score 17 more runs than Boston. The biggest storyline in this series is unquestionably the status of Aaron Judge. Just over a week after returning from an injury that robbed him of more than three months of the season, Judge hit the IL with an injury that Aaron Boone said was pretty serious and Judge said wouldn’t cause him to miss playoff games.

So, we’ll see what state the slugger is in for this series and for however long New York is alive in their quest for their 28th championship and first since 2009. What we do know is that the Yankees, who have had their playoff ticket punched for a while, have their rotation set up with presumptive AL Cy Young Award winner Cam Schlitter, followed by Max Fried and Gerrit Cole.

The Yankees were 41-25 with Judge and 52-43 without him, so they weren’t some ruined ballclub without 99 in the lineup, but obviously you’d prefer to have him and have him in good health at this time of the year. 

Ironically, the turning point of the season for the Red Sox came against the Yankees. The date was June 25 and the Red Sox had just lost a series to the Rockies to fall to 32-46. Plane troubles forced the team’s charter to circle back to Denver International Airport, where they would be stuck until the next morning with a four-game series against the Yankees set to start that night and Schlittler on the mound. The Red Sox won 6-3, swept the series, and went 55-29 from the hellacious travel day on.

Now a best-of-three will determine who moves on to face the AL East champion Tampa Bay Rays.

Red Sox vs. Yankees Wild Card Round Odds

Yankees -170 // Red Sox +140

Total Games: 2.5 (-105/-115)

Red Sox vs. Yankees Wild Card Round Schedule

*all games in New York

Game 1: Tuesday, September 29, 8 p.m. ET (NBC)

Game 2: Wednesday, September 30, 8 p.m. ET (NBC)

Game 3: Thursday, October 1, 8 p.m. ET (NBC) – if necessary

Red Sox vs. Yankees Offense

Edge: Yankees

I like a lot of the pieces and parts of the Red Sox lineup, but the playoffs are about hitting the long ball. The Yankees finished the regular season second in dingers with 223. Conversely, only the Brewers hit fewer home runs than the Red Sox among playoff teams. The Red Sox hit the same number of home runs (164) as the Guardians. That’s not the company that you want to keep offensively, especially in that department.

While the Yankees only had one guy with 20+ HR, they had 11 guys hit at least 10 HR. In the 13 games against the Red Sox, though, they only hit 15 homers and slashed just .232/.290/.370. Boston pitchers allowed the fewest home runs in the league with 155. They had the third-lowest HR/FB% against. That will be the key to this series. If the Red Sox can keep the Yankees in the ballpark and neutralize their biggest offensive advantage, this series has the potential to look a lot different.

The other thing worth considering is what these two teams have done since the Red Sox got hot. Remember that June 25 date I mentioned above? The Red Sox were eighth in wOBA and 11th in wRC+ from that time through the end of the regular season. The Yankees? 28th in wRC+ and 28th in wOBA. Collectively, when adjusted for park factor and the league run-scoring environment, the Red Sox were 4% above league average offensively and New York was 12% below league average.

With more left-handed power in the Bronx, and more power overall, the Yankees still get the edge in this department in my mind, but without Judge or with Judge at 70-80%, it’s not a dramatic edge.

Red Sox vs. Yankees Pitching

Edge: Neither

The Red Sox have a very good pitching staff, but Schlitter, Fried, and Cole in a three-game series is a lot for any team to overcome. Even with the Red Sox rotation improving greatly during the course of the season thanks to Payton Tolle, Jake Bennett, and a return to normalcy for Ranger Suarez, I give New York the slight edge. Sonny Gray has had one of the best seasons of his career and he and Tolle are two very different arms to get in the first two games of this series. Suarez is a big part of Boston’s home run prevention.

Schlittler had a 1.80 ERA over his final 75 innings in the regular season with a .161/239/.253 slash against and just a .226 wOBA. He struck out 102 and walked just 24 while allowing just four homers. However, Fried missed time twice this season and has worked just 26.1 innings since coming back from a second absence. Cole has a 4.98 ERA with a 5.05 xERA and a 5.61 FIP over his last six starts.

I do have some workload concerns about Tolle, but he pitches well beyond his years and he, Gray, and Suarez all wound up with outstanding regular-season numbers, so much so that the Red Sox were eighth in starting pitcher ERA. The Yankees led the league, but beyond Schlittler, I’m concerned enough to not consider them as the team with the edge.

These two teams were first and second in reliever ERA, with Boston first and New York second. The Red Sox also had the lowest FIP as a relief corps, with their focus on home run prevention as the biggest separator relative to the rest of the league. There is no doubt that Schlittler is the best pitcher in the series, but the Red Sox arguably have the better depth. And, like the Yankees, they clinched early enough to set things up how they want.

Red Sox vs. Yankees Miscellaneous Notes

The health of Ceddanne Rafaela is a big deal here. He recently came off the IL and then tweaked his leg injury again in the series against Cleveland. He did play a little bit over the weekend against the Cubs. Rafaela is +21 Defensive Runs Saved and teammate Wilyer Abreu is +27 DRS. Cody Bellinger is also +21 DRS for the Yankees. But, the Red Sox are the better defensive team and a lot of it has to do with the outfield defense. Given how well the Yankees run the bases, limiting hits is key for the outfielders.

Austin Wells has also graded as one of the best pitch-framing catchers in the league this season. Backup catcher Ali Sanchez has been great as well. One of the reasons Boston acquired Adley Rutschman was for his framing defense. We should have some good work behind the dish in this series.

Aaron Boone is no stranger to the postseason, but he is just 25-27 in his nine years with the Yankees. Chad Tracy took over for Alex Cora, who was fired after a 10-17 start, and was 77-58 in the regular season, but the 41-year-old is in the postseason for the first time, as he worked his way up the organization into this role.

Red Sox vs. Yankees Prediction

Pick: Red Sox +140

While I do believe that the Yankees win this series, the gap between these two teams is not as large as this line would imply. Yes, Schlitter is a very tough customer in Game 1, but Gray or Tolle could turn it into a battle of the bullpens, at which point the Red Sox are going to be in the game. Also, while the Yankees bullpen was good for the season, they aren’t entering the playoffs in top-notch form, posting a FIP in the 4.70s for September.

Also, the Yankees do need to flip a switch of sorts here, while the Red Sox had to scratch and claw to get back into the race and then clinch their spot in the postseason over the final week and a half. The Yankees have been a playoff team pretty much since the start of the season.

Other series previews: Phillies vs. Braves | White Sox vs. Astros | Cubs vs. Padres