NY Yankees vs Pittsburgh Pirates Prediction 7/21/26 MLB Picks Today

The Pittsburgh Pirates and the New York Yankees meet Monday in MLB action from Yankee Stadium. We will look at this from a betting perspective and determine the best bets for this game. Here’s a Pittsburgh Pirates vs. New York Yankees prediction.

Starting Pitching Matchup

The Pittsburgh Pirates will send out Bubba Chandler for the start here and Chandler is 3-8 with a 4.77 ERA and 85 strikeouts this season. Will Warren will get the nod for the Yankees and is 7-4 with a 4.03 ERA and 96 strikeouts this season.

Pittsburgh Pirates Recap

The Pittsburgh Pirates come into this game looking to bounce back from an 8-5 loss at the hands of the New York Yankees to sit at 52-49 this season. After this series, the Pirates will head home for a series against the Chicago Cubs.

Pirates Alternate Wins & Losses In 4 Straight

Oneil Cruz has 66 hits including 10 doubles, 14 home runs and 44 RBIs while Ryan O’Hearn has 90 hits with 13 doubles, 16 home runs and 64 RBIs this season. Nick Gonzales has 110 hits with 17 doubles and 45 RBIs while Brandon Lowe has 90 hits with 21 doubles, 21 home runs and 65 RBIs and Bryan Reynolds has 103 hits with 24 doubles, 2 triples, 14 home runs and 59 RBIs as well this season.

New York Yankees Recap

The New York Yankees come into this game looking to add on to their win over the Pirates to sit at 56-44 this season. After this series, the Yankees will head on the road for a series against the Philadelphia Phillies.

Yankees Win 6 Of Last 8

Ben Rice has 99 hits with 17 doubles, 29 home runs and 68 RBIs and Aaron Judge has 53 hits with 10 doubles, 17 home runs and 38 RBIs. Cody Bellinger also has 92 hits with 19 doubles, 3 triples, 11 home runs and 52 RBIs. Jazz Chisholm Jr. also has 76 hits with 13 doubles, 16 home runs and 43 RBIs as well on the year.

Pittsburgh Pirates @ New York Yankees Betting Trends: July 21, 2026

• Probable Starting Pitcher: Will Warren      Record this season: 7-4      ERA: 4.03
• Home Record: 4-2
• Last 5 against Pirates: 0-0

Why the New York Yankees will win

• The Pirates have lost seven of their last eight road games against AL East opponents.
• The Yankees have won each of their last five games after playing the previous day.
• The Yankees have covered the run line in seven of their last eight games.
• The Pirates have failed to cover the run line in six of their last seven night games against teams that held a winning record.
• The Yankees have won the first inning in four of their last five night games against National League opponents that held a winning record.
• The Pirates have trailed after 3 innings in seven of their last eight road night games.
• The Yankees have led after 5 innings in eight of their last nine night games against NL Central opponents.

• Probable Starting Pitcher: Bubba Chandler      Record this season: 3-8      ERA: 4.77
• Road Record: 1-5
• Last 5 against Yankees: –

Why the Pittsburgh Pirates will win

• The Pirates have won each of their last four games as underdogs against American League opponents following a road loss.
• The Yankees have lost six of their last seven games as home favorites after playing the previous day.
• The Pirates have covered the run line in each of their last seven games as underdogs against AL East opponents following a loss.
• The Yankees have failed to cover the run line in seven of their last eight home games after playing the previous day.
• The Pirates have won the first inning in three of their last four games as underdogs against AL East opponents.
• The Pirates have led after 3 innings in three of their last four games against AL East opponents that held a winning record.
• The Pirates have led after 5 innings in eight of their last nine games against American League opponents that held a winning record.

Total Runs Facts

• Each of the last six games between the Pirates and Yankees have gone OVER the total runs line.
• Each of the Pirates’ last four games after playing the previous day have gone OVER the total runs line.
• There has been at least one run scored in the first inning in each of the Pirates’ last six games against AL East opponents.
• There has been at least one run scored in the first inning in each of the Yankees’ last four games as home favorites.

New York Yankees Player Prop Facts

• Jazz Chisholm has hit at least one home run in three of his last four home appearances against the Pirates.
• Will Warren has recorded six or more strikeouts in six of his last seven home appearances.
• Ben Rice has recorded at least one hit in each of the Yankees’ last 14 games against opponents that held a winning record.
• Ben Rice ranks 2nd amongst qualified players for Slugging Percentage (.594) this season.

Pittsburgh Pirates Player Prop Facts

• Esmerlyn Valdez has hit a home run in five of the Pirates’ last six games as underdogs.
• Bubba Chandler has recorded five or more strikeouts in four of his last five appearances in night games against teams that held a winning record.
• Nick Gonzales has recorded at least one hit in each of the Pirates’ last 10 road games.
• Nick Gonzales ranks 5th amongst qualified players for Batting Average (.309) this season.

Matchup/League Facts

• The Yankees rank 1st in the league for ERA this season (3.42).
• The Yankees rank 1st in the league for ERA this season (3.42).
• The Pirates rank 1st in the league for hits this season (923).
• The Pirates rank 1st in the league for hits this season (923).

Pittsburgh Pirates vs. New York Yankees Prediction

I’m on the over in this game. I don’t trust either starting pitcher as far as I can throw them in this game, and I think this is going to be a game where you bring a glove to the ballpark. Chandler’s had control issues and the Yankee bats are waking up, but Will Warren’s also been more than hittable in a lot of his recent outings. Give me the over here.