Last year, the Yankees and Red Sox met in an AL Wild Card Series that seemed like it could easily go either way. Of course, it went to a decisive Game 3, where Cam Schlittler delivered a monster outing, and the teams have gone in opposite directions since.
This year, the Yankees — while you can have your qualms about their play and the roster construction — are again a contender and enter this weekend with the best record in the American League. Meanwhile, the Red Sox have fallen way off the pace and are last in both the division and the AL as a whole, recently crashing past the Angels. Interim skipper Chad Tracy’s club is still missing big-name players like Garrett Crochet and Roman Anthony, and their offense has been appallingly anemic. Entering play yesterday, only the underachieving Padres had a worse hitting corps by wRC+ (86 to Boston’s 89), and the Red Sox were also second-worst by total homers (65 in 77 games).
However, the two teams are now set to meet this weekend at Fenway Park. While the “throw out the record books when rivals meet” is too much of a cliché, we’ve seen the Yankees put in some iffy performances of late and the Red Sox still do have talent. With four games coming over the next couple days, let’s take a look at the probable pitching matchups for this series.
Thursday: Cam Schlittler vs. Connelly Early (7:10 pm ET)
The opening game of the series will be a rematch of Game 3 of the Wild Card Series last year. Schlittler began June with his first genuinely not-great start of the season, and has since responded by looking like his normal dominant self. He’s allowed just two earned runs combined over his last three outing, and struck out 13 batters during his last time out against the Reds. That’s a career best for him, besting even the aforementioned Wild Card Series Game 3.
Early was somewhat famously the man opposite Schlittler last year, as he was also notably a rookie getting a start in that massive game. His overall numbers in 2026 grade out as either side of average, depending on what stat you’re looking at. He has been hit by the home run bug a bit this year, having given up 14 in 15 starts, so that’ll be something the Yankees will hope they can take advantage of.
Friday: Will Warren vs. Payton Tolle (7:10 pm ET)
Warren’s numbers for the season are absolutely ones that you’ll take from a back-end starter; however, he often looks like he has the raw stuff to be even better than that. However, he just has too many starts like the last two, where he’s given up a total of 16 hits, even if he’s only been dinged for four earned runs in that time.
The Yankees have only gotten one previous look at the second-year Tolle, and it didn’t go well. Back in April, he struck out 11 batters while holding the Yankees to just one run on three hits. That being said, after a very good start — even beyond that outing — to his sophomore campaign, Tolle has struggled a bit recently. His ERA is 5.29 over his last three games, with his overall season mark going up nearly an entire run in the process.
Saturday: Gerrit Cole vs. Jake Bennett (1:10 pm ET)
Following a brilliant initial return from Tommy John surgery, Cole has looked a bit pedestrian of late. Returning from an injury that knocks you out for a full year is always going to produce some up-and-down results, but you’d like to see Cole fare better than the 5.95 ERA he’s produced over his last four appearances.
The Red Sox will be going with yet another youngster on Saturday, and this will be the Yankees’ first ever meeting with the rookie Bennett. He’s been decent so far in his career, and his coming off his best-ever major-league performance. Earlier this week against the Rockies, he shut out Colorado over six innings, allowing four hits, while striking out nine.
Sunday: Carlos Rodón vs. Sonny Gray (7:20 pm ET)
A 114 ERA+ with a FIP that suggests he could be a bit better is absolutely something worth taking from Rodón, especially considering that he’s probably the Yankees No. 4 when everyone is healthy. However, especially with his walks, he can often be a chore to watch. The Red Sox are one of the teams that walk the least in all of MLB, so theoretically, this is a chance to put in a good effort on that front.
The veteran and former Yankee Gray has been a bright spot for the Red Sox this year, with a 2.95 ERA over his 14 starts so far (and might already be on the trade block due to Boston’s spiral). One of those came against the Yankees back at the start of the month, where he and the Red Sox got the win. That wasn’t his best effort of the season, but he did manage to frustrate the Yankees enough for them to get just three runs despite eight hits.
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