Back-to-back wins over the Tigers have the Yankees back on track as June enters its final stretch. Aaron Boone's club now has a three-game lead over the Rays in the American League standings, putting the Yankees in a good spot to continue their momentum-building road trip when they meet the rival Red Sox for a four-game series at Fenway Park, beginning on Thursday. It will be the third series of the 2026 campaign between the AL East rivals. The Yankees swept the Red Sox at Fenway Park in late April before the pair each won once, with another postponed, during a three-game encounter in the Bronx earlier this month. The Red Sox are 5-10 since that encounter, while the Yankees are 10-5, which encapsulates how each respective season is going. Although they've had the Red Sox's number more often than not so far this season, that isn't stopping the Yankees from sending their best four (healthy) starters to Boston this week. Here are the starting pitching matchups for each contest, as well as who has the edge. Thursday, June 25 (7:10 p.m. ET): Cam Schlittler (NYY) vs. Connelly Early (BOS)While some players crumble under the pressure that rivalries bring, that isn't the case for Cam Schlittler when facing the Red Sox. The AL Cy Young favorite has already dog-walked Boston twice this season, being credited for one win with 10 strikeouts while limiting the opposition to two earned runs on eight hits and a pair of walks. That success dates back to the 2025 postseason, when Schlittler struck out a whopping 12 Red Sox batters over eight scoreless innings in Game 3 of the AL Wild Card. Cam Schlittler has 4 strikeouts through 3 innings so far against the Red Sox pic.twitter.com/Qyts7aGOPy— SNY Yankees (@snyyankees) June 7, 2026Including his last meeting against the Red Sox (June 7), Schlittler now owns a 0.96 ERA in his last three starts, which includes another shutout performance over six innings vs. the Reds last week. Clearly, he doesn't intend to slow down. Schlittler will try to outpitch Connelly Early, who's had a rocky June, to say the least (1-3, 5.66 ERA in 20 2/3 innings). He did limit the Mariners to one earned run with seven strikeouts in six innings to end a personal three-game skid last week, so it remains to be seen if a turnaround has actually begun. Having said that, the Yankees already beat Early back on April 21, taking him for three earned runs on five hits as he issued three walks in 5 1/3 innings. Throw in the fact that he's at a disadvantage with the Yankees owning the second-best OPS vs. lefties (.787), and it's easy to see why Schlittler is more than capable of winning this duel. Game 1 pitching advantage: Yankees Friday, June 26 (7:10 p.m. ET): Will Warren (NYY) vs. Payton Tolle (BOS)As June winds down, Will Warren is still looking for his first win of the month. He's been a fairly middle-of-the-road pitcher lately, with a 0-1 record and 4.50 ERA in his last three outings, which includes allowing six runs—but only two earned—and eight hits over 5 2/3 innings against the Reds last Saturday. Things haven't been promising, but Warren can rest easy knowing that he's 3-0 with a 2.97 ERA in seven road starts this season. At the same time, his last trip to Boston (Sept. 14, 2025) ended in disaster, giving up six ERs on 10 hits in a 6-4 loss to the Red Sox. In fact, he owns an all-time 9.42 ERA in three career clashes against New York's AL East nemesis. Can Will Warren continue his road success? Or will his past struggles vs. the Red Sox reemerge this weekend? | Wendell Cruz-Imagn ImagesThe Yankees are more than familiar with Payton Tolle, who struck them out a season-high 11 times back on April 23. Yes, New York ultimately won that night, but it only managed to score one earned run off Tolle until he left the game after six innings. The memories from that encounter are still relatively fresh; however, there might not be much of a reason to fear the Red Sox's hurler at the moment. That's because Tolle has lost each of his last three starts, allowing 10 earned runs and three homers in 17 innings—good for a 5.29 ERA. He also has only one win in six starts at Fenway Park this season, which includes games where the Red Sox only scored three-plus runs twice. With Warren struggling vs. the Red Sox and Tolle lacking support at home, this starting pitching battle is more of a crapshoot. Game 2 pitching advantage: even Saturday, June 27 (1:10 p.m. ET): Gerrit Cole (NYY) vs. Jake Bennett (BOS)The only afternoon game of the four-game series will see Gerrit Cole go one-on-one with Jake Bennett on Saturday. Cole has been solid for the most part after missing all of 2025 due to injury, but his last outing was by far his worst of the year. The former AL Cy Young winner conceded all five earned runs in 4 1/3 innings in the Yankees' 5-3 loss to the Tigers in Monday's series opener. After pitching 12 2/3 scoreless innings in May, Cole now has a 5.95 ERA in four appearances across June (19 2/3 frames). And that's without mentioning that the Red Sox have been Cole's kryptonite lately. He's 0-3 with a 7.92 ERA in his last six games against Boston, also allowing between three and five earned runs on each of his last five trips to Fenway. Success has eluded Gerrit Cole during the Yankees starter's recent trips to Boston. Will that change on Saturday afternoon? | Vincent Carchietta-Imagn ImagesMeanwhile, the Red Sox's Jake Bennett is off to a solid start to his first MLB season. Despite a 1-3 record across five starts, the former Oklahoma Sooner boasts a 3.71 ERA and is coming off a solid effort against the Rockies on Monday, when he struck out a career-high nine batters without allowing a run in six innings. Bennett has momentum, but he's also inexperienced and is about to face a Yankees squad that knows how to hit off left-handed pitchers. With the Red Sox also averaging only 2.3 runs in the 25-year-old southpaw's last three starts, this game should be Cole's to lose, regardless of his recent woes. Game 3 pitching advantage: Yankees Sunday, June 28 (7:20 p.m. ET): Carlos Rodon (NYY) vs. Sonny Gray (BOS)Carlos Rodón has usually given the Yankees an edge whenever he's taken to the mound this season. While that's still true for most nights, the three-time MLB All-Star won't have an easy time outlasting Sonny Gray, who leads the American League with nine wins while posting his best ERA (2.95) of the last three seasons. Sonny Gray has been dominant this season, even beating the Yankees once. | David Dermer-Imagn ImagesGray already bested the Yankees at the start of June, earning the win while surrendering three earned runs on eight hits with three strikeouts. He's now 2-1 with a 3.94 ERA in his five most recent clashes with New York, demonstrating the consistency he's known for. At the same time, Rodón has been consistent in his own way. He owns a 2-3 record and 3.97 ERA in six career trips to Boston, averaging 11.9 strikeouts per nine innings. This season, he hasn't lost an appearance since May 21, going 4-0 with a 3.49 ERA and 29 strikeouts in 28 1/3 innings in his last five games. Gray has been the better pitcher overall this season, but Rodón's recent results can't be ignored. Still, it's hard to go against the former when he's only lost once this season and has already proved to have the Yankees' number. Game 4 pitching advantage: Red Sox This series has the potential for four solid pitching matchups, but the edge goes to the Yankees. Yes, Boston's rotation has been solid, too, but the Red Sox are in a slump and have struggled to consistently provide their pitching staff with adequate run support. It might not be the highest-scoring series, but New York should still get the job done. Overall series advantage: YankeesAdd us as a preferred source on GoogleFollow