Boston Red Sox vs Pittsburgh Pirates Prediction 8/14/2026 Today’s MLB Picks

The Boston Red Sox and the Pittsburgh Pirates meet Friday in MLB action from PNC Park. We will look at this from a betting perspective and determine the best bets for this game. Here’s a Boston Red Sox vs. Pittsburgh Pirates prediction.

Starting Pitching Matchup

The Boston Red Sox will send out Jake Bennett for the start here and Bennett is 7-5 with a 3.17 ERA and 55 strikeouts this season. Pittsburgh will send out Bubba Chandler here and Chandler is 5-8 with a 4.26 ERA and 103 strikeouts this season.

Boston Red Sox Recap

The Boston Red Sox come into this game looking to add on to their 7-0 win over the Blue Jays from Thursday to sit at 65-56 this season. After this series, the Red Sox will head home for a series against the Diamondbacks.

Red Sox Snap Five-Game Slide

Wilyer Abreu leads the Red Sox with 114 hits including 24 doubles, 3 triples, 21 home runs and 64 RBIs while Ceddanne Rafaela has 132 hits with 28 doubles, 3 triples, 16 home runs and 63 RBIs and Caleb Durbin’s added 97 hits with 22 doubles, 12 home runs and 60 RBIs as well. Jarren Duran has 88 hits with 13 doubles, 3 triples, 16 home runs and 61 RBIs as well this season. Willson Contreras has added 107 hits with 19 doubles, 24 homers and 72 RBIs of his own on the year.

Pittsburgh Pirates Recap

The Pittsburgh Pirates come into this game looking to add on to their 13-1 win over Miami last time out to sit at 59-64 this season. After this series, the Pirates will take on the Detroit Tigers in a series at home.

Pirates Snap Three-Game Skid

Oneil Cruz has 66 hits including 10 doubles, 14 home runs and 44 RBIs while Ryan O’Hearn has 97 hits with 15 doubles, 17 home runs and 69 RBIs this season. Nick Gonzales has 137 hits with 21 doubles and 53 RBIs while Brandon Lowe has 113 hits with 25 doubles, 25 home runs and 74 RBIs and Bryan Reynolds has 118 hits with 28 doubles, 2 triples, 15 home runs and 63 RBIs as well this season.

Boston Red Sox @ Pittsburgh Pirates Betting Trends: August 14, 2026

• Probable Starting Pitcher: Bubba Chandler      Record this season: 5-8      ERA: 4.26
• Home Record: 3-3
• Last 5 against Red Sox: –

Why the Pittsburgh Pirates will win

• The underdogs have won nine of the last 10 games between the Red Sox and Pirates.
• The Red Sox have lost each of their last seven night games against NL Central opponents following a road win.
• The Red Sox have failed to cover the run line in each of their last 11 Friday night games as favorites against National League opponents.
• The Pirates have covered the run line in each of their last seven games as home underdogs against American League opponents.
• The Pirates have led after 5 innings in each of their last five home games against American League opponents.
• The Pirates have led after 3 innings in each of their last seven games as home underdogs against American League opponents.
• The Pirates have won the first inning in three of their last four home games against AL East opponents.

• Probable Starting Pitcher: Jake Bennett      Record this season: 7-5      ERA: 3.17
• Road Record: 3-2
• Last 5 against Pirates: –

Why the Boston Red Sox will win

• The Red Sox have won each of their last 11 Friday games.
• The Pirates have lost each of their last seven night games against AL East opponents following a win.
• The Pirates have failed to cover the run line in each of their last eight games following a win.
• The Red Sox have covered the run line in each of their last 12 Friday games.
• The Red Sox have led after 5 innings in each of their last nine Friday games as favorites.
• The Red Sox have led after 3 innings in each of their last 11 Friday games.
• The Red Sox have won the first inning in five of their last six night games against National League opponents.

Total Runs Facts

• Eight of the Red Sox’s last nine games as road favorites have gone UNDER the total runs line.
• Five of the Pirates’ last six night games as underdogs have gone UNDER the total runs line.
• There has been at least one run scored in the first inning in each of the Red Sox’s last eight games at PNC Park.
• There has been at least one run scored in the first inning in each of the last six night games between the Red Sox and Pirates at PNC Park.

Pittsburgh Pirates Player Prop Facts

• Esmerlyn Valdez has hit a home run in three of the Pirates’ last four games as home underdogs.
• Bubba Chandler has recorded a win in each of his three previous home appearances against AL opponents.
• Bubba Chandler has recorded five or more strikeouts in five of his last six appearances in night games against teams that held a winning record.
• Bryan Reynolds has recorded at least one hit in each of the Pirates’ last seven home games.
• Nick Gonzales ranks T4th in the league in Hits (137) this season.

Boston Red Sox Player Prop Facts

• Ceddanne Rafaela has hit at least one home run in each of the Red Sox’s last three games against NL opponents.
• Jake Bennett has recorded five or more strikeouts in three of his last four appearances in night games against teams that held a losing record.
• Jake Bennett has recorded a win in six of his last eight appearances.
• Ceddanne Rafaela has recorded at least one hit in each of the Red Sox’s last 16 road games against opponents that held a losing record.
• Willson Contreras ranks 6th amongst qualified players for On Base Percentage (.389) this season.

Matchup/League Facts

• The Pirates rank 1st in the league for hits this season (1090).
• The Pirates rank 30th in the league for strikeouts against this season (1159).
• The Red Sox rank 1st in the league for runs allowed this season (452).
• The Red Sox rank 3rd in the league for doubles this season (217).

Boston Red Sox vs. Pittsburgh Pirates Prediction

I’m on the Pirates in this one. I just think that the Red Sox with that torrid run in July might’ve peaked too early and now the fall off happens. The Pirates need to start fighting to get themselves back in the hunt in the NL race and I think they show up at home here. Give me Pittsburgh.

Chris Ruffolo's Pick: Pittsburgh +115