Boston Red Sox vs NY Yankees Prediction 6/27/26 MLB Picks Today

The New York Yankees and the Boston Red Sox meet Saturday in MLB action from Fenway Park. We will look at this from a betting perspective and determine the best bets for this game. Here’s a New York Yankees vs. Boston Red Sox prediction.

Starting Pitching Matchup

The New York Yankees will send out Gerrit Cole for the start and Cole is 2-2 with a 3.62 ERA and 29 strikeouts this season. Jake Bennett will start for the Red Sox and is 1-3 with a 3.71 ERA and 22 strikeouts this season.

New York Yankees Recap

The New York Yankees come into this game looking to bounce back from a 6-1 loss at the hands of the Red Sox on Saturday to slip to 48-33 on the year. After this series, After this series, the Yankees will head home for a series against the Detroit Tigers.

Yankees Drop Back-To-Back Games

Ben Rice has 79 hits with 15 doubles, 22 home runs and 53 RBIs and Aaron Judge has 53 hits with 10 doubles, 17 home runs and 38 RBIs. Cody Bellinger also has 77 hits with 16 doubles, 3 triples, 11 home runs and 49 RBIs. Jazz Chisholm Jr. also has 62 hits with 10 doubles, 12 home runs and 33 RBIs as well on the year.

Boston Red Sox Recap

The Boston Red Sox come into this game looking to add on to their victory over the Yankees from Friday to improve to 34-46 this season. After this series, the Red Sox will take on the Washington Nationals in a series at home.

Red Sox Pushing For Series Win

Wilyer Abreu leads the Red Sox with 81 hits including 16 doubles, 2 triples, 10 home runs and 38 RBIs while Trevor Story has 34 hits with 7 doubles, 3 homers and 19 RBIs and Marcelo Mayer’s added 45 hits with 10 doubles, 3 home runs and 22 RBIs as well. Roman Anthony has 25 hits with 5 doubles, a triple, a home run and 5 RBIs so far this season while Jarren Duran has 58 hits with 9 doubles, 12 home runs and 37 RBIs as well this season. Willson Contreras has added 76 hits with 13 doubles, 16 homers and 46 RBIs of his own on the year.

New York Yankees @ Boston Red Sox Betting Trends: June 27, 2026

• Probable Starting Pitcher: Jake Bennett      Record this season: 1-3      ERA: 3.71
• Home Record: 1-2
• Last 5 against Yankees: –

Why the Boston Red Sox will win

• The Yankees have lost four of their last five games as favorites.
• The Red Sox have won each of their last four games as home underdogs against AL East opponents following a home win.
• The Yankees have failed to cover the run line in each of their last five games as favorites.
• The Red Sox have covered the run line in eight of their last nine games as underdogs against AL East opponents following a home win.
• The Yankees have trailed after 5 innings in each of their last five games as favorites.
• The Red Sox have won the first inning in three of their last four games.
• The Red Sox have led after 3 innings in three of their last four games.

• Probable Starting Pitcher: Gerrit Cole      Record this season: 2-2      ERA: 3.62
• Road Record: 1-1
• Last 5 against Red Sox: 0-3

Why the New York Yankees will win

• The Yankees have won each of their last eight day games against American League opponents.
• The Red Sox have lost each of their last six day games against AL East opponents.
• The Red Sox have failed to cover the run line in each of their last six day games against AL East opponents.
• The Yankees have covered the run line in each of their last four day games against AL East opponents.
• The Yankees have won the first inning in four of their last five games as favorites against the Red Sox at Fenway Park.
• The Red Sox have trailed after 3 innings in six of their last seven games as home underdogs against American League opponents.
• The Red Sox have trailed after 5 innings in each of their last six day games against AL East opponents.

Total Runs Facts

• Five of the Yankees’ last six games have gone UNDER the total runs line.
• Five of the Red Sox’s last six home games against AL East opponents have gone UNDER the total runs line.
• There has been no run scored during the first inning in each of Jake Bennett’s five previous appearances as a starter.
• There has been no run scored during the first inning in each of the Yankees’ last five day games against AL East opponents.

Boston Red Sox Player Prop Facts

• Caleb Durbin has hit at least one home run in three of the Red Sox’s last five games against opponents that held a winning record.
• Ceddanne Rafaela has recorded at least one hit in each of his last 12 appearances in day games.

New York Yankees Player Prop Facts

• Jose Caballero has hit a home run in each of the Yankees’ last two games as favorites against AL East opponents.
• Gerrit Cole has recorded a win in each of his last four road appearances against AL East opponents.
• Gerrit Cole has recorded six or more strikeouts in 18 of his last 19 appearances in day games against AL teams that held a losing record.
• Jasson Dominguez has recorded at least one hit in each of his last nine appearances against AL East opponents.
• Jazz Chisholm ranks T3rd in the league in Steals (24) this season.

Matchup/League Facts

• The Red Sox rank 30th in the league for RBIs this season (305).
• The Red Sox rank 29th in the league for runs scored this season (319).
• The Yankees rank 1st in the league for home runs this season (120).
• The Yankees rank 1st in the league for ERA this season (3.32).

New York Yankees vs. Boston Red Sox Prediction

I’m backing Boston here. If you told me a year ago I’d be backing Jake Bennett against Gerrit Cole, I’d think you’re crazy. That being said, Boston’s easily been the better team in the first two games of this series and Yankees/Red Sox is always one of those sets where records can be meaningless and these teams just want to beat each other. I think it’s more of that here so I’m rolling with the Red Sox for another W here.