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

By: Eddie Kline Published 06/27/2026, 12:50 AM ET

Yankees Preview

The Saturday MLB schedule will get underway with a rivalry game between the New York Yankees and the Boston Red Sox from Fenway Park. Be ready for the baseball season with all of our MLB predictions. The Yankees (48-33) are eight games above .500 on the road and are in possession of a one-game lead over Tampa Bay for the top spot in the AL East Division. Last night, SP Will Warren (7-2) gave up five runs in five plus innings in New York’s 6-1 road loss against Boston.

2023 American League Cy Young Award winner Gerrit Cole (2-2 3.62 ERA) will make his sixth start of the year for the Yankees. Last time out, Cole (4.1 IP) was roughed up for nine hits and five runs during a 5-3 road loss against Detroit.

Red Sox Preview

The Boston Red Sox are a major league worst 11 games below .500 at home and are trapped in the AL East Division basement. During Friday’s home victory 1B Willson Contreras went 2-for-3 with a home run and two RBIs to lead the Boston offense. SP Payton Tolle (4-5) fanned seven batters across seven frames to earn the win for the Red Sox (34-46).

Interim Boston manager Chad Tracy will turn to twenty-five year old lefty Jake Bennett (1-3 3.71 ERA) on Saturday. Through 26 plus innings, Bennett has allowed just one long ball and fanned 22 batters while posting a solid 1.13 WHIP.

Subscribe Now

I authorize Picks And Parlays to send me promotional emails

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

Terms & Conditions

Yankees vs Red Sox Pick

New York OF Aaron Judge suffered a stress fracture in his right rib cage and will be out until after the All-Star Break. Through 81 games, New York ranks 2nd in OPS and 5th in runs scored. For the season, Boston ranks 25th in OPS and 29th in runs scored. Take the Yankees to win on the road. Final Score Prediction, New York Yankees win 6-2.

Never Tried Picks and Parlays? Now Is Your Chance

Get your first daily picks package for ONLY $1 using coupon code BUCK
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.

Min. Deposit $5

Cashable No

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.

Requirement New Users – Bet $5 Get $200 in Bet Reset Tokens for 5 Days. (Up to $1,000 Bet Reset Tokens)

Cashable No

Gambling Problem? Call 1-800-GAMBLER or 1-800-MY-RESET. Call 1-888-789-7777 or visit ccpg.org/chat (CT). Hope is here. GamblingHelplineMA.org or call (800) 327-5050 for 24/7 support (MA). Visit www.mdgamblinghelp.org (MD). Call 1-877-HOPENY or text HOPENY (467369) (NY). 21+ (18+ DC, IA, KY, WV) only. New users only or text HOPENY (467369) (NY). Casino, First online real money wager only. $5 first deposit required. Min $5 wager required for 5 consecutive days. Bonus issued as non-withdrawable Bet Reset tokens. Refund from token issued as nonwithdrawable bonus bet that expire 7 days after receipt. Max refund $200 per day. Restrictions apply, including token expiration. See full terms at fanduel.com/sportsbook. Call 1-877-770-7867 (LA).

Min. Deposit $5

Odds Requirements -500

Cashable No

GAMBLING PROBLEM? CALL 1-800-GAMBLER or 1-800-MY-RESET, (800) 327-5050 or visit gamblinghelplinema.org (MA). Please Gamble Responsibly. 888-789-7777/visit ccpg.org (CT), or visit www.mdgamblinghelp.org (MD), 1-800-981-0023 (PR). 21+ and present in most states. (18+ DC/NH/PR/WY). Void in CAN. Eligibility restrictions apply. On behalf of Boot Hill Casino (KS). Pass-thru of per wager tax may apply in IL. 1 per new DraftKings customer. $5+ first-time bet req. Max. $200 issued as non-withdrawable Bonus Bets that expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 7/19/26 at 11:59 PM ET. Sponsored by DK.