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Boston Red Sox at New York Yankees Game 2 prediction, pick for Wednesday 9/30/26

Boston Red Sox at New York Yankees Game 2 prediction, pick for Wednesday 9/30/26

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By: Griffin Wong

Last season, the Boston Red Sox and the New York Yankees faced off in the AL Wild Card series, but after taking Game 1 at Yankee Stadium, the Red Sox proceeded to lose Games 2 and 3 behind a brilliant Game 3 performance from then-rookie Cam Schlittler. It was the sixth time that the historic Northeast rivals have faced off in the postseason, but the first series that the Yankees had won since 2003.

After another dominant performance from Schlittler, who’s likely to win the AL Cy Young Award, New York is one game away from putting Boston away and claiming its fourth series victory over its rival in seven tries. Game 2 will begin at 8 p.m. ET in the Bronx.

Last night was a battle of youngsters, but tonight, the veterans will take the mound. Sonny Gray will get the ball for the Red Sox, and the Yankees will turn to Max Fried.

Let’s break down this latest installment of baseball’s most famous rivalry with some odds and lines at DraftKings Sportsbook.

Boston Red Sox at New York Yankees Game 2 Best Bets

  • New York Yankees -1.5 (+136): It’s hard to have any faith in Boston, which lost 9-0 yesterday and had the worst scoring offense in MLB in September. New York had its own offensive travails towards the end of the season, but the Yankees are in better form right now.
  • Under 6.5 (+101): Last night’s game was on track to go under the total until the Red Sox’s relievers surprisingly imploded, but they still have a few strong relievers (Garrett Whitlock, Garrett Crochet, and Aroldis Chapman) yet to pitch who could follow the still-elite Gray.

Boston Red Sox at New York Yankees Game 2 prediction, preview

After a white-hot 27-3 stretch in the middle of the season, Boston limped to the finish line, going just 12-12 in September, and in that span, it had comfortably the league’s worst offense. The Red Sox’s malaise didn’t improve in Game 1; former top prospect Roman Anthony, whose sophomore campaign was limited to just 55 games because of injuries, left early with a hand issue, and Adley Rutschmann, acquired at the trade deadline for a steep price to (unsuccessfully) buoy the offense, went just one-for-four. Willson Contreras, who was an MVP candidate for much of the season but posted just a .750 OPS after the start of August, went zero-for-four and struck out thrice. To be fair, the fact that Boston’s pitching struggled so much came as somewhat of a surprise, given that its bullpen posted a 2.15 mark in September, but even if the Red Sox pitch better tonight — they should, with Garrett Whitlock, Aroldis Chapman, Jake Bennett, and 2025 AL Cy Young Award runner-up Garrett Crochet likely available — their offense will need to step up much more than they have.

Over New York’s closing stretch, it was better, going 15-8 in September, and while its offense in that span was still poor by its standards, a tie for 14th in OPS isn’t as damaging as Boston’s mark. The Yankees’ offense came to play in Game 1; Ben Rice slumped badly throughout late July and August, but he slashed .313/.453/.597 in his final 20 games of the season and carried that form over into this series, hitting two homers to account for six of New York’s eight RBI’s. Plus, George Lombard Jr., who got his career off to a hot start before slowing down in September, managed a three-hit game in his postseason debut. That production from the offense turned out to be more than enough, as the Yankees were expectedly brilliant on the mound: Schlittler pitched 6.1 innings of two-hit ball across 117 pitches, and Paul Blackburn and John Schreiber shut it down. New York’s staff as a whole had a sub-3 ERA after the All-Star break, and star relievers Brent Headrick and David Bednar have yet to take the mound. Will Warren, a starter who finished eighth in Rookie of the Year voting last season, could also be available.

The Red Sox should have a chance with Gray on the mound as long as its bullpen holds up. The 36-year-old has enjoyed a renaissance season, pitching to a 2.72 ERA across 29 starts and leading all of baseball with 18 wins, and he’ll likely receive Cy Young Award votes for the fourth time in his career. However, advanced numbers paint a much more mixed picture of him, as his 3.87 xERA is only a 60th-percentile mark. To be fair, Gray could be well-suited to combat one of the Yankees’ biggest strengths, as he sports a 77th-percentile chase rate and New York has operated a fairly disciplined plate approach. He’s also been good at avoiding walks, and the Yankees have drawn among the most free passes. However, Gray ranks in just the 33rd percentile in whiff rate and the 35th percentile in average exit velocity, and New York has recorded the second-highest average exit velocity in the league this season. The Yankees have also been much better at home, owning the eighth-best home OPS in baseball. Gray was stellar in his lone home start against New York, but at Yankee Stadium, he allowed three earned runs in 6.1 outings, a good-but-not-great performance.

Fried should have a slight edge in the starting pitching matchup. Injuries limited him to only 20 starts this season, but he made the most of them, pitching to a 2.80 ERA. In fact, across a seven-start stretch in August and early September, he allowed no more than one earned run in any start, recording a 1.49 mark across that span. Advanced numbers suggest that he got unlucky not to have been even better, as he ranks in the 98th percentile in xERA and the 97th in pitching run value. Boston’s offense isn’t built to take advantage of Fried’s few weaknesses, as while he sports a below-median chase rate and whiff rate, the Red Sox have a fairly aggressive batting approach and below-average contact skills. Plus, Fried has been among baseball’s best at limiting hard contact, as he has a top-ventile barrel rate, hard-hit rate, and average exit velocity, and Boston ranks near the bottom of the league in each of those stats. His comparative struggles at Yankee Stadium could be offset by the Red Sox’s quiet offense away from Fenway Park, and he’s pitched well against his rival this season regardless of venue. He only threw 3.2 innings the last time he faced this lineup at home, but he was still solid, giving up just one earned run.

Boston Red Sox at New York Yankees Game 2 pick, best bet

Best Bet: New York Yankees -1.5 (-136)

Boston’s red-hot summer stretch vaulted it into the postseason, but beyond that, the Red Sox didn’t play like a playoff team for much of the season. They certainly don’t look like one now, offensively, and Fried isn’t a much worse hurler than Schlittler.

Strong Lean: Under 6.5 (+101)

Although Game 1 went over the total late because the youngsters in Boston’s bullpen experienced their rookie lumps in quick succession, I trust the Red Sox’s bullpen overall, and I trust Gray. This series deserves at least one proper pitcher’s duel.

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Griffin Wong has been a content writer at DK Network since November 2024. Prior to that, he was the former sports editor for the Harvard Crimson, where he covered the football team for two years and earned four Story of the Year nominations from the Associated College Press. A lifelong Lakers and Dodgers fan, Griffin’s favorite athlete of all time is Kobe Bryant. When he’s not writing, Griffin is usually skiing, running, golfing, or playing basketball — badly.
Disclaimer

I am a promoter at DraftKings and am also an avid fan and user and may sometimes play on my personal account in the games that I offer advice on. Although I have expressed my personal view on the games and strategies above, they do not necessarily reflect the view(s) of DraftKings and do not constitute a representation that any particular strategy will guarantee success. All customers should use their own skills and judgment in building lineups. I may also deploy different players and strategies than what I recommend above. I am not an employee of DraftKings and do not have access to any non-public information.