New York Yankees vs. Boston Red Sox: Series Preview

Way back at the start of the season, the Yankees and Red Sox faced off on equal footing. New York took two of three in that contest, and haven’t seen sight of Boston since — either physically, or in the standings. This is the first time since Opening Weekend that the two will meet up, and the first time all year that they’ll clash in Fenway.

The Yankees took off about a week after that initial series, rocketing to the top of the MLB standings where they’ve sat ever since. The Red Sox, meanwhile, were briefly competing with the Orioles for last place in the AL East. They finished April with a dismal 9-14 record and treaded water in May, but from the start of June they got hot and climbed back into the playoff picture. They had two separate seven-game win streaks that month and went 20-6 overall ... good enough to still lose a game in the standings because of the Yankees’ absurd 22-6 mark in that same month.

Still, their hot month has gotten Boston right back into the thick of things, briefly giving them a hold of second place in the division. A poor start to July and a lost series to the Rays now has them in a tie for second, which is where they are entering play today. Now the Yankees will get their second crack at them, and these are the pitching matchups you can expect to see:

DraftKings series odds: Yankees win (+135); Red Sox win (+310); Tie (+160)

Thursday: Gerrit Cole vs. Josh Winckowski (7:10 p.m. EST)

Gerrit Cole’s season has been defined by mistake pitches — when he’s on he’s very much the ace that the Yankees were looking for when they signed him, but then a stray pitch finds the middle of the plate and suddenly he’s served up another homer. Cole’s allowed 14 long balls already this year, and often that’s the only way to score off of him. Aside from his clunker in Minnesota, however, Cole was excellent in June and has gotten his numbers in line with expectations — a 2.99 ERA and 3.42 FIP with 117 strikeouts in 93.1 innings. Cole’s last outing was another solid one, going six innings and allowing two runs on, surprise, two solo homers.

Josh Winckowski gets the honor of being the first Boston starter to tackle the Yankees’ lineup, and he’s been a recent addition to the Red Sox rotation. Winckowski made his debut on May 28th and got rocked by Baltimore, allowing four runs in three innings, but since then he’s been pretty solid. In all three of his June starts he went at least five innings and allowed two runs or less, and he threw a quality six innings in his first start of the month against the Cubs as well. Winckowski’s a four-pitch pitcher, featuring a four-seam fastball, a cutter, a slider, and a changeup with a heavy emphasis on the four-seamer and slider.

Friday: Nestor Cortes vs. TBD (7:10 p.m. EST)

Nasty Nestor had been riding a fast track to the All-Star Game until June came around, and the crafty lefty hit his first bump in the road. There wasn’t an implosion of an outing to point to, but a series of so-so starts with questionable command started to pile up after a dominant seven-inning gem against the Angels at the beginning of the month. Cortes bounced back to start July, tossing six innings of one-run ball against the Guardians, and he’ll look to get back in a groove here against the Sox. For the season, Cortes is rocking a still-phenomenal 2.44 ERA with a more modest 3.36 FIP to go along with 91 strikeouts in 85 innings.

The Red Sox rotation has been in a chaotic state for a bit, and they don’t have an announced starter for either Friday or Saturday. Friday’s options are a bit clearer though, as Alex Cora mentioned that Michael Wacha should be in line to start as long as everything is good after he was scratched from his slotted Monday outing. Wacha has turned back the clock this season after a couple of bad years with the Mets and Rays, and is sporting a 2.69 ERA and 3.96 FIP for Boston. He’s struck out 50 batters in 70.1 innings, good for a career-low 6.40 K/9.

Saturday: Jordan Montgomery vs. TBD (7:15 p.m. EST)

Montgomery has been perhaps the most consistent of the Yankees’ starters, outside of a blip in the radar towards the end of June. Monty served up a couple of poor outings against the Rays and Athletics, allowing four and five runs respectively in starts where one big inning early constituted most of the damage (though he still managed to give the team length, going at least six inning in both appearances). His most recent outing against Cleveland was more promising — he went five innings and posted a season-high eight strikeouts while allowing just one run. Montgomery’s got a 3.19 ERA and 3.75 FIP on the season to go with 72 strikeouts in 90.1 innings.

Once again the Red Sox don’t have a starter listed for this game. In this spot in the rotation last time, Cora opted to go for an opener in Austin Davis and a bulk pitcher in Kutter Crawford, and it’s possible they opt for a similar method again. For what it’s worth, Crawford has pitched to a 5.04 ERA and 4.19 FIP in 25 innings, but most of his runs allowed came early in the year as a middle reliever. Since getting stretched out, Crawford’s posted outings of five innings with no runs allowed, four innings with four runs allowed, and 5.1 innings with no runs allowed.

Sunday: Jameson Taillon vs. Nick Pivetta (7:08 p.m. EST)

Taillon’s season appeared to be reaching new heights at the start of June, when he posted back-to-back two-hit gems, the latter of which was a perfect game bid until the eighth inning. Since then, the wheels have fallen off of Taillon’s once-brilliant season: he’s allowed 21 runs in 26.2 innings over six starts, never making it past the fifth inning in any of them. His ERA has ballooned from 2.30 to 3.63 in that time, derailing what was a probable All-Star bid unless he can get on track fast. The lowly Pirates roughed up their former pitcher in his last outing, scoring five in 5.1 innings of work.

Back in line with a regular starter, Pivetta’s been solid for the Red Sox since coming over from Philadelphia in 2020. His major improvement has been managing to keep the ball in the yard more, pitching to a career-best 0.9 HR/9 so far, and it’s resulted in a very dependable 3.68 ERA and 3.65 FIP for Pivetta to pair with 95 strikeouts in 100.1 innings. He did get rocked in his last outing, a seven-run fiesta against the Rays, so we’ll see if he gets things back under control against the Bombers.