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Boston Red Sox vs NY Yankees Prediction 4/21/26 MLB Picks Today

NY Yankees (13-9) vs. Boston Red Sox (9-13)
April 21, 2026 6:45 pm EDT
The Line: Boston Red Sox -108 / NY Yankees -112; Over/Under: 8.5
(Get latest betting odds)

The New York Yankees and the Boston Red Sox meet Tuesday 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 Luis Gil here and Gil is 0-1 with a 7.00 ERA and 7 strikeouts this season. In his last five starts against Boston, Gil is 2-1 with a 0.99 ERA and 26 strikeouts. Connelly Early will start this one for Boston and is 1-0 with a 2.29 ERA and 20 strikeouts this season. This will be Early’s first career start against the Yankees.

New York Yankees Recap

The New York Yankees come into this game looking to build on their 7-0 win over the Royals last time out to sit at 13-9 this season. After this series, the Yankees will head on the road again for a series against the Houston Astros.

Yankees Win 3 In A Row

Giancarlo Stanton has 18 hits with 3 doubles, 2 home runs and 10 RBIs while Ben Rice has 22 hits with 6 doubles, 8 home runs and 18 RBIs and Aaron Judge has 19 hits with 3 doubles, 9 home runs and 16 RBIs. Cody Bellinger also has 21 hits with 3 doubles, a triple, 3 home runs and 11 RBIs. Jazz Chisholm Jr. also has 12 hits with 5 doubles as well on the year.

Boston Red Sox Recap

The Boston Red Sox come into this game looking to add on to their 8-6 win over Detroit last time out to sit at 9-13 this season. After this series, the Red Sox will head on the road for a series against the Baltimore Orioles.

Red Sox Salvage Split Vs. Tigers

Wilyer Abreu leads the Red Sox with 24 hits including 4 doubles, a triple, 3 home runs and 11 RBIs while Trevor Story has 18 hits with 5 doubles, 2 homers and 17 RBIs and Marcelo Mayer’s added 10 hits with 3 doubles, a home run and 3 RBIs as well. Roman Anthony has 18 hits with 3 doubles, a triple, a home run and 4 RBIs so far this season while Jarren Duran has 11 hits with 3 doubles, a home run and 10 RBIs as well this season. Willson Contreras has added 20 hits with 2 doubles, 4 homers and 12 RBIs of his own on the year.

New York Yankees @ Boston Red Sox Betting Trends: April 21, 2026

 

  • Probable Starting Pitcher: Connelly Early      Record this season: 1-0      ERA: 2.29
  • Home Record: 0-0
  • Last 5 against Yankees: 0-1

Why the Boston Red Sox will win

  • The Yankees have lost each of their last four games as favorites against AL East opponents.
  • The Red Sox have won each of their last six Tuesday games as underdogs against AL East opponents.
  • The Yankees have failed to cover the run line in each of their last five road games against AL East opponents.
  • 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 3 innings in five of their last six games at Fenway Park against opponents that held a losing record.
  • The Yankees have trailed after 5 innings in five of their last six games at Fenway Park against opponents that held a losing record.

 

  • Probable Starting Pitcher: Luis Gil      Record this season: 0-1      ERA: 7.00
  • Road Record: 0-1
  • Last 5 against Red Sox: 2-1

Why the New York Yankees will win

  • The Red Sox have lost each of their last five home games against American League opponents following a home win.
  • The Yankees have won four of their last five games.
  • The Red Sox have failed to cover the run line in each of their last six home games against American League opponents following a win.
  • The road team has covered the run line in four of the Red Sox’s last five games.
  • The Red Sox have trailed after 5 innings in eight of their last nine night games against American League opponents.
  • The Red Sox have lost the first inning in four of their last five night games against American League opponents.
  • The Yankees have led after 3 innings in four of their last five games.

Total Runs Facts

  • Seven of the Red Sox’s last eight games as underdogs against AL East opponents have gone UNDER the total runs line.
  • Each of the Yankees’ last five games as favorites against the Red Sox have gone UNDER the total runs line.
  • The ‘Inning 1 OVER 0.5 runs’ market has hit in 14 of the Yankees’ last 15 games at Fenway Park.
  • The ‘Inning 1 OVER 0.5 runs’ market has hit in 13 of the last 14 night games between the Yankees and Red Sox at Fenway Park.

Boston Red Sox Player Prop Facts

  • Wilyer Abreu has hit a home run in each of his last two appearances with the Red Sox as home underdogs against AL East opponents.
  • Masataka Yoshida has recorded at least one hit in each of the Red Sox’s last 10 games against AL East opponents.

New York Yankees Player Prop Facts

  • Aaron Judge has hit at least one home run in five of the Yankees’ last eight games.
  • Cody Bellinger has recorded at least one hit in each of his last eight appearances.
  • Ben Rice ranks 1st amongst qualified players for Slugging Percentage (.800) this season.

Matchup/League Facts

  • The Red Sox rank T29th in the league for home runs this season (13).
  • The Red Sox rank 27th in the league for slugging percentage this season (.345).
  • The Yankees rank 2nd in the league for steals this season (27).
  • The Yankees rank T2nd in the league for walks this season (109).

New York Yankees vs. Boston Red Sox Prediction

I’m on the Boston Red Sox here. I just think that this is the best rivalry in baseball, and the Red Sox, no matter how bad they may be in a certain season, will always give the Yankees their best and get a matchup with Gil, who I’m still not sold on this season. On the flipside, New York’s going against Early here and the Yankees haven’t been overly convincing against lefties for a good chunk of the year so far and I think the Red Sox take advantage here. Give me Boston.

Chris Ruffolo's Free Pick: Boston Red Sox -108

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Chris Ruffolo

Chris joined the Sports Chat Place team in August 2016 and has a proven system that combines multiple analytical and situational statistics and trends to give out thousands of winning picks over the last three years with winning records across all of the top leagues, Follow Chris Ruffolo on Twitter @ruffthepickdawg

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