Yankees vs Red Sox Prediction, Picks & Odds for Today's MLB Game

Todd Cordell - Betting Analyst at Covers.com
Todd Cordell • Betting Analyst 12+ years betting experience
Updated: Jun 27, 2026 , 09:16 AM ET • 4 min read

Jake Bennett limits a banged-up New York Yankees offense on Saturday.

MLB

Match starts: 2 hrs
NYY
70 %
BOS
30 %
EXPERT PICK - MONEYLINE
Boston +105 Boston +105
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Boston Red Sox MLB Jake Bennett
Photo By - Reuters Connect. Boston Red Sox pitcher Jake Bennett.

The Boston Red Sox took the first two games against their biggest rivals.

While the Yankees are -125 favorites to take Game 3, my Yankees vs. Red Sox predictions and MLB picks believe the value lies in backing Boston to clinch a series victory on Saturday, June 27.

Who will win Yankees vs Red Sox today: Red Sox moneyline (+105)

Injuries have taken real punch out of the New York Yankees' offense, especially against left-handed pitching.

They have really tailed off in June, ranking 19th in wOBA and 20th in OPS, while striking out at the sixth-highest rate.

It’ll be tough for them to get going against Jake Bennett, who sits in the 97th percentile in xERA through the first handful of starts in his career.

Gerrit Cole has not been his dominant self, ranking in the 52nd percentile in Pitcher Run Value and allowing 13 runs over his past four starts.

Back the Boston Red Sox to -110.

Covers COVERS INTEL: The Yankees are clearly missing the power from their lineup, sitting 28th in hard hit rate against left-handed pitching in June.

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Yankees vs Red Sox Over/Under pick: Under 8.5 (-110)

This total is a little high for me. 

Bennett has generated grounders at an elite rate while also avoiding walks, which should allow him to neuter a powerful Yankees offense.

Cole’s elite strikeout stuff has simply not been there but he has still found a way to be effective, posting an xERA of 3.5 or lower in four of six starts.

The Red Sox are 26th in wOBA vs. right-handed pitching this month, so they’re a team Cole should be able to work his way through even lacking punchouts. 

Play the Under to -125.

Todd Cordell's 2026 Transparency Record
  • ML/RL bets: 44-32, +3.20 units
  • Over/Under bets: 40-32-4, +3.99 units

Yankees vs Red Sox weather

Temperatures in the mids 70s are expected but with slight winds blowing inwards. Neutral hitting conditions.

Yankees vs Red Sox odds

  • Moneyline: Yankees -125 | Red Sox +105
  • Run line: Yankees -1.5 (+135) | Red Sox +1.5 (-155)
  • Over/Under: Over 8.5 (-110) | Under 8.5 (-110)

Yankees vs Red Sox trend

The Yankees have hit the Under in 29 of the last 50 away games (+8.10 units, 15% ROI). Find more MLB betting trends for Yankees vs. Red Sox.

How to watch Yankees vs Red Sox and game info

Location Fenway Park, Boston, MA
Date Saturday, June 27, 2026
First pitch 1:10 p.m. ET
TV ABC
Yankees starting pitcher Gerrit Cole
(2-2, 3.62 ERA)
Red Sox starting pitcher Jake Bennett
(1-3, 3.71 ERA)

Yankees vs Red Sox latest injuries

Odds are correct at the time of publishing and are subject to change.
Not intended for use in MA.
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Todd Cordell - Covers
Betting Analyst

Todd Cordell is a data-driven betting analyst. He uses numbers to help identify value across a wide variety of sports, with NHL being his specialty. Shot props, in particular, have proven to be a very fruitful market. Todd has served as a betting analyst in the public sphere for many years, most recently with theScore covering the NHL and MLB.

When not writing about sports betting, Todd stays busy analyzing the New Jersey Devils with a fine-tooth comb for InfernalAccess, his Devils-centric blog. Todd attended Sheridan College and graduated in 2014 with a diploma in print journalism.

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