Liam MacKenzie – Treasurer/Sports Editor
The Bronx, NY – The rivalry is back in October. For the second consecutive year, the Boston Red Sox and New York Yankees will meet in the American League Wild Card Series, bringing one of baseball’s most historic rivalries back to the postseason stage. The best-of-three showdown begins Tuesday night at Yankee Stadium, where every pitch will carry the weight of another chapter in the long-standing battle between Boston and New York.
There is no shortage of history between these two franchises, but this matchup adds another layer to the rivalry. After the Yankees ended Boston’s postseason run last year, the Red Sox now have another chance to take down their biggest rival when it matters most, with a trip to the American League Division Series against the Tampa Bay Rays waiting for whoever comes out on top.
Game 1: Tolle vs. Schlittler – The series begins tonight, September 29, at 8:00 p.m. Eastern Time from Yankee Stadium. Rookie left-hander Payton Tolle will take the mound for Boston, while New York will counter with right-hander Cam Schlittler, who started Game 3 of last year’s Wild Card Series for the Yankees.
Tolle enters the postseason after finishing his rookie campaign with a 9-6 record, a 3.03 ERA and 171 strikeouts. He has already shown that he can handle New York, allowing just one run over 13 innings across two starts against the Yankees this season while striking out 18.
Schlittler has established himself as one of the Yankees’ most important young pitchers. The 14-6 right-hander posted a 1.95 ERA with 239 strikeouts during the regular season, giving New York a formidable arm to open the series.
For Boston, the key will be finding a way to get Schlittler early and give Tolle some breathing room. With the series opening on the road, a strong start could be especially important for the Red Sox as they look to take home-field advantage away from New York.
Game 2: Gray vs. Fried – Game 2 is set for Wednesday, September 30, with Boston scheduled to turn to veteran right-hander Sonny Gray. Gray finished the regular season 18-5 with a 2.72 ERA and 149 strikeouts while leading the Red Sox with 20 quality starts.
Gray will face Yankees left-hander Max Fried, who went 5-5 with a 2.80 ERA during the regular season. Fried has already faced Boston twice this year, including an eight-inning scoreless performance at Fenway Park in April.
Gray’s connection to New York adds another layer to the matchup. The veteran spent time with the Yankees earlier in his career, and now he will have the opportunity to help Boston against his former team in a postseason game.
The importance of Game 2 will depend on the result of Tuesday night’s opener. A Red Sox victory would give Boston a chance to close out the series, while a Yankees win would put the pressure on Boston to avoid elimination and force a decisive Game 3.
Game 3: If Necessary – If neither team has won twice after the first two games, the rivalry will move to a winner-take-all Game 3. Boston is scheduled to send left-hander Ranger Suárez to the mound, while New York would counter with right-hander Gerrit Cole.
Suárez finished the regular season 8-5 with a 3.22 ERA and 140 strikeouts, while Cole went 10-9 with a 3.61 and 131 strikeouts. Both pitchers bring significant experience to what would be the biggest game of the series.
For Boston, Suárez’s postseason experience could become particularly important in a deciding game. The left-hander has made eight career postseason starts and owns a 1.48 career postseason ERA, giving the Red Sox an experienced option if the series goes the distance.
Players to Watch – For Boston, Roman Anthony will be one of the biggest names to watch as he enters his first postseason matchup against the Yankees. The 22-year-old finished the regular season strongly and will be part of a Red Sox lineup that also features Adley Rutschman, Willson Contreras, Ceddanne Rafaela and Caleb Durbin, giving the Red Sox several different ways to create offense throughout the lineup.
Rafaela could be especially important because of his ability to impact the game on both sides of the ball, while Durbin has already provided Boston with a spark against New York this season. Meanwhile, Aroldis Chapman could play a major role late in games, particularly given his history with the Yankees and experience pitching in high-pressure postseason situations.
New York will have plenty of players Boston’s pitching staff will need to account for as well. Ben Rice enters the series after hitting 41 home runs during the regular season, while Cody Bellinger provides another experienced bat in the middle of the Yankees’ lineup. George Lombard Jr. and Jazz Chisholm Jr. are also capable of creating problems on the bases and putting pressure on Boston’s defense.
With Aaron Judge unavailable for the Wild Card Series, the Yankees will need players such as Rice, Bellinger and Chisholm to help carry the offensive load. In a series where one swing can change the game, both lineups have several players capable of making their presence felt when the pressure is at its highest.
A Rivalry Renewed – The Red Sox and Yankees have already faced each other 13 times this season, with New York winning seven games and Boston taking six. The Yankees Stadium, where all three games of the Wild Card Series will be played.
This will be the seventh postseason meeting between the two franchises, with their previous six playoff matchups split evenly. Last year’s Wild Card Series added another chapter to the rivalry, and now Boston gets another opportunity to change the ending.
What’s at Stake – There is little room for error in a best-of-three series. Boston needs two victories to move on, while New York will be trying to protect its home field and earn another trip to the American League Division Series.
Game 1 gets underway tonight at 8:00 p.m. ET, with Game 2 scheduled for Wednesday night as the series continues. If the Red Sox and Yankees split the first two games, a winner-take-all Game 3 will follow Thursday. One of baseball’s most recognizable rivalries is back on the postseason stage, and this time, a trip to the ALDS is on the line.

