Yankees Vs. Red Sox: Breaking Down The Wild Card Series Pitching Matchups

We’re in store for the next chapter of the storied rivalry between the New York Yankees and Boston Red Sox.

The Yankees and Red Sox posted the second- and third-best regular season records in the American League in 2026, and will now face off in the AL Wild Card round beginning on Tuesday, Sept. 29. 

The pitching matchups for the three-game series were revealed on Monday, and feature a likely Cy Young winner as well as a past recipient, multiple impressive young pitchers and 15 combined All-Star nods among the six starters.

The series, which will go to three games if necessary, will be played in its entirety at Yankee Stadium as New York was the top AL wild-card team. The winner will face the Tampa Bay Rays in the American League Division Series.

Game 1 features Yankees’ starter Cam Schlittler, the favorite for the 2026 AL Cy Young Award thanks to an AL-leading 1.95 ERA and 215 ERA+ over 33 starts and 193 ⅔ innings. Schlittler struck out 239 batters – 11.1 per nine – in his sophomore campaign, nearly five times as many punch outs as free passes. Schlittler was behind only Brewers’ ace Jacob Misiorowski in ERA, second in wins above replacement (7.0), tied for third in strikeouts, fourth in innings and second in adjusted ERA+.

There wasn’t a better starting pitcher in the AL in 2026 than Cam Schlittler. (Photo by Michael Urakami/MLB Photos via Getty Images)

Opposing the Massachusetts native on the mound is another second-year starter, Payton Tolle. The 6-foot-6 left-hander made 26 starts and threw 148 ⅔ innings, striking out 10.4 batters per nine with a strikeout-to-walk ratio of 4.3. By wins above replacement, Tolle was the second-most valuable pitcher on Boston’s staff; part of that is due to injuries – not a single Red Sox starter made 30 starts – but Tolle’s own accomplishments played a role as well.

Wild Card Series G2

Fried vs. Gray

Max Fried will take the mound for New York in Game 2, and manage to be worth 3.7 WAR in just 112 ⅔ innings and 20 starts: Fried was placed on the IL twice in 2026 with a bone bruise in his throwing elbow. He’s looked as dominant as usual since his return on Aug. 29, posting a 2.73 ERA across five starts while holding opponents to a single run in four of those.

Sonny Gray has been solid in his first year in Boston. (Photo by Scott Taetsch/Getty Images)

Sonny Gray, in his first year with the Red Sox, was the team’s best starter. He led the majors with 18 wins and the AL in winning percentage, but these stats were not inflated by Boston’s success: Gray led the team in WAR (4.7) and posted a 2.72 ERA over 29 starts and 169 innings. While his strikeout-to-walk ratio dipped from 2025’s NL-leading mark of 5.3, Gray made up for the additional free passes and lost strikeouts by limiting opponents to 7.9 hits per nine. The result? An ERA+ of 150 and Gray’s best season since 2023.

Wild Card Series G3

Cole vs. Suarez

Gerrit Cole didn’t return to the Yankees until May 22, following the Tommy John surgery that cost him the entire 2025 season. Cole was not his past Cy Young-caliber self – he won the AL award in 2023 with New York – but still produced a 3.61 ERA over 127 innings. The only issue with Cole is that he has been homer-prone once again – it’s an issue that occasionally pops up for the righty, who is now 36 and post-Tommy John.

Ranger Suarez, in his first season with the Red Sox after signing a five-year, $130 million deal with Boston this past offseason, made 28 starts and produced a 3.22 ERA. His 126 ERA+ was right along his career line that earned him that contract in the first place – the big question is whether or not that will be enough against Cole, if he’s at his finest… or if it will be necessary at all, since Boston has to win one of the first two games on the road to force a Game 3 in the first place.