New York Yankees vs. Boston Red Sox, Picks and Prediction, Saturday, June 27, 2026

By: Bosun Akinpelu Published 06/27/2026, 05:35 AM ET
Yankees vs. Red Sox prediction
Use Code WWWC

New York (48-32) will be trying to increase their lead in the AL East when they visit Fenway Park on Saturday afternoon to face Boston (33-46) in the third game of their four-game series at 1 PM. ET. Read on to find out which team picks up the win in this Yankees vs. Red Sox prediction. Don’t go down on strikes! Get our top MLB Predictions and increase your bankroll!

Gerrit Cole, 2-2, 3.62 ERA, will get the start for the Yankees. The Red Sox will counter with Jake Bennett, 1-3, 3.71 ERA.

Yankees Going For Second Consecutive Series Win

The Yankees bounced back from their series loss to the Reds with a series win over the Tigers. They currently lead the AL East, with a two-game lead over the Rays, and will try to increase their division lead with a win on Saturday.

New York averages 5.06 runs per game, which is fourth in the league. Their .244 batting average is 15th in the league. Their .329 on base percentage is sixth, while their .437 slugging percentage is seventh.

Get Free $30 Credit for Premium Picks + Exclusive Discounts

Subscribe Now

I understand that I can unsubscribe at any time. I have read and accepted the Terms & Conditions and Privacy Policy. I consent that Winners and Whiners may use third-party services to process my data.

Ben Rice has been the most consistent batter for the Yankees. He leads the team with a .281 batting average, 22 home runs, and 53 RBI.

New York is giving up 3.63 runs per game, which is second in the league. Opponents have a .226 batting average against the Yankees, which is fourth in the league. Their 3.34 ERA leads the league, while their 1.18 WHIP is third.

In his last start, Cole gave up nine hits and five runs in 4.1 innings, leading to a 5-3 loss to Detroit. He is 7-6 with a 5.42 ERA in 21 games against Boston.

Red Sox Trying To Bounce Back From Series Loss

The Red Sox followed up their series win over Seattle with a series loss to Colorado. They will try to bounce back from the series loss and cut into New York’s division lead when they play on Saturday.

Boston averages 3.94 runs per game, which is 29th in the league. Their .244 batting average is 17th in the league. Their .312 on base percentage is 23rd, while their .385 slugging percentage is 26th.

Ceddanne Rafaela leads Boston with a .286 batting average, while Willson Contreras leads the team with 16 home runs and 46 RBI.

Boston is giving up 4.03 runs per game, which is seventh in the league. Opponents have a .246 batting average against the Red Sox, which is 19th in the league. Their 3.82 ERA is seventh, while their 1.26 WHIP is 12th.

In his last start, Bennett gave up four hits and no runs in six innings, but the team lost to the Rockies 3-2.

Yankees vs. Red Sox Picks

Money Line Pick for Yankees vs. Red Sox

  • Boston Red Sox ML (4 Units)

The Red Sox have the advantage in this game because they’re playing well offensively and have scored at least five runs in their last three games. They’ve been solid against right-handers, and they’re going up against Cole, who struggled on the mound in recent starts, giving up nine runs in his last three starts. He gave up 17 runs in his last three starts against the Red Sox and will have a hard time slowing them down.

The Yankees will have a hard time keeping up offensively because they have struggled offensively in recent games, scoring 11 runs in their last three games. They’ve hit the ball well against left-handers, but they’re going up against Bennett, who gave up seven runs in his last three home starts, so expect him to keep their offense in check. Take Boston on the money line.

Over/Under Pick for Yankees vs. Red Sox

  • Over (4 Units)

The Yankees average 5.06 runs per game. They’re batting .256 against left-handers, and they’re facing a starter who gave up six runs in his last three starts. The Red Sox average 3.94 runs per game. They’re batting .234 against right-handers, and they’re going up against a starter who gave up 11 runs in his last two starts against them. Expect these teams to score enough runs to push the score over the total.

Never Tried Winners and Whiners? Now Is Your Chance

  • Get your first daily picks package for ONLY $1 using coupon code DOLLAR
  • If the pick loses, we credit your account with 3 Flex Picks
  • If the pick wins, we still give you 1 Flex Pick on the house
  • Win or lose, you walk away ahead. One dollar. No catch.
  • Check out more MLB predictions
BetMGM Sport

Up To $1500 in Bonus Bets Paid Back if your First Bet Does Not Win

Show Bonus Code
Claim Bonus
Signup Promo Recommended BetMGM Sport Bonus
Min. Deposit $5
Cashable No
FanDuel Sportsbook

New Users – Bet $5 Get $200 in Bet Reset Tokens for 5 Days

Show Bonus Code
Claim Bonus
Signup Promo Hot Offer FanDuel Sportsbook Bonus
Requirement New Users – Bet $5 Get $200 in Bet Reset Tokens for 5 Days. (Up to $1,000 Bet Reset Tokens)
Cashable No
DraftKings Sport

New DraftKings Customers: Spend $5+ Get $200 in Bonuses Instantly!

Show Bonus Code
Claim Bonus
Signup Promo Hot Offer DraftKings Sport Bonus
Min. Deposit $5
Odds Requirements -500
Cashable No

If you or someone you know has a gambling problem, crisis counseling and referral services can be accessed by calling 1-800-GAMBLER (1-800-426-2537) (IL). Gambling problem? Call 1-800-GAMBLER (MI/NJ/PA/WV/WY), 1-800-9-WITH-IT (IN), 1-800-522-4700 (CO), 1-800-BETS OFF (IA), 1-888-532-3500 (VA), 1-800-NEXT STEP (AZ), or call/text TN REDLINE 1-800-889-9789 (TN). 21+ (18+ WY). AZ/CO/IL/IN/IA/MI/NJ/PA/TN/VA/WV/WY only. Eligibility restrictions apply. T&C's Apply. Void where prohibited. If you click on a link on this site which takes you to a bookmaker or casino and you subsequently open an account, Pick and Parlays may receive a commission. Bets placed are the responsibility of the bettor.

Copyright © 2026 Picks and Parlays. All rights reserved.

The sports news and information contained at this site is for entertainment purposes only. Any use of this information in violation of laws whether they are federal, state and/or local is prohibited. Picks and Parlays is the nation's premier resource for sports betting and handicapping information.

Sign Up Get $30 Premium Picks Credit + Exclusive Offers
Special Offer
Up To $1500 in Bonus Bets Paid Back if your First Bet Does Not Win
Play now Gambling problem? Call 1-800-GAMBLER or 1-800-MY-RESET (Available in the US) 877-8-HOPENY or text HOPENY (467369) (NY) 1-800-327-5050 (MA), 1-800-BETS-OFF (IA), 1-800-981-0023 (PR). 21+ only. Please Gamble Responsibly. See BetMGM.com for Terms. First Bet Offer for new customers only (if applicable). Subject to eligibility requirements. Bonus bets are non-withdrawable. In partnership with Kansas Crossing Casino and Hotel. Promotional offers not available in Mississippi, New York, Ontario, or Puerto Rico.