Get Expert Player Predictions for Pirates vs Red Sox – Friday August 29, 2025

Pittsburgh Pirates

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Boston Red Sox

As the Boston Red Sox prepare to face off against the Pittsburgh Pirates on August 29, 2025, at Fenway Park, they do so with momentum on their side after a narrow 3-2 victory in their previous encounter. The Red Sox, currently boasting a solid 75-60 record, have established themselves in the playoff race, while the Pirates, at 59-76, are struggling significantly this season.

On the mound, the Red Sox are projected to start Tolle, a left-handed pitcher ranked 94th among MLB starters. Tolle’s projections suggest he will struggle, with averages showing he could allow 2.3 earned runs over 5.0 innings, which is above average for him, alongside a concerning 4.7 hits allowed. This could be a challenge against an offense that ranks 8th overall in MLB and has shown they can capitalize on pitching weaknesses.

Opposing him is the Pirates’ Paul Skenes, a right-hander and the 2nd best pitcher in MLB per the leading MLB projection system. Skenes is having an outstanding year with a 2.07 ERA and is coming off a fantastic performance where he pitched 7 innings with no earned runs, 7 strikeouts, and only 3 hits. Although he projects to struggle slightly with his hits and walks allowed, it’s likely his elite strikeout ability will give him an edge against a high-strikeout Red Sox lineup.

Betting markets indicate a close game, with the Red Sox set at -115 and the Pirates at -105 on the moneyline. This matchup comes with a low Game Total of 7.5 runs, suggesting a pitcher’s duel is anticipated. Given Skenes’ elite status and Tolle’s average performance, the Red Sox will need to rely on their powerful offense to put runs on the board against a Pirates team that ranks 29th offensively.

Pittsburgh Pirates Insights

• Paul Skenes – Over/Under 17.5 Pitching Outs (-115/-115)
  Compared to average, Paul Skenes has been granted more leash than the average pitcher this year, throwing an additional 4.0 adjusted pitches each start.
  Explain: Pitchers with a longer leash are more likely to go deeper into games and record more outs.
• Tommy Pham – Over/Under 0.5 Hits (-230/+175)
  Tommy Pham is projected to hit 4th in the lineup in this matchup, which would be an upgrade from his 54% rate of hitting in the bottom-half of the lineup this year.
  Explain: The higher in the order a player bats, the more plate appearances he will get and the more opportunities he will get to hit the Over for every market. A player who hits higher in the order than he normally does may provide extra value opportunity since the market may be based on him hitting lower.
• Henry Davis – Over/Under 0.5 Total Bases (-160/+125)
  Henry Davis pulls many of his flyballs (36.4% — 93rd percentile) and sets up very well considering he’ll be hitting them towards the game’s shallowest LF fences today.
  Explain: This player’s skill set matches up particularly well with the park he’s in today, which may lead to better-than-usual performance.

Boston Red Sox Insights

• Tolle – Over/Under 5.5 Strikeouts (+115/-150)
  Due to his reverse platoon split, Payton Tolle will benefit from being matched up with 9 bats in the projected lineup who bat from the opposite side in this matchup.
  Explain: A pitcher with a reverse platoon split will perform better against opposite-handed hitters (i.e. a right-handed pitcher will be better against a left-handed hitter). Holding this advantage against several hitters can have a huge impact on whether a pitcher will perform well or struggle on any given day.
• Jarren Duran – Over/Under 1.5 Total Bases (+115/-150)
  Jarren Duran is guaranteed to hold the advantage against every reliever the entire game as none of the available options for the Pittsburgh Pirates share his handedness.
  Explain: Hitters perform worse against pitchers of the same handedness (i.e. righty-vs-righty), and being able to avoid those matchups against the bullpen boosts performance and creates hidden edge.
• Rating 3rd-least steep in baseball this year, Boston Red Sox batters as a group have recorded a 12° launch angle on their hardest-contacted balls (a reliable metric to evaluate power skills).
  Explain: If you hit the ball hard but straight at the ground, it doesn’t do you any good. A player that is skilled at lifting his hardest hit balls into the air stands the best chance of turning them into extra-base hits or home runs.

Betting Trends

• Boston Red Sox – Moneyline (-115)
  The Boston Red Sox have hit the Moneyline in 43 of their last 68 games (+16.55 Units / 18% ROI)
• Pittsburgh Pirates – Over/Under 3.5 Team Total (-130/+100)
  The Pittsburgh Pirates have hit the Team Total Under in 43 of their last 63 away games (+21.70 Units / 29% ROI)
• Jared Triolo – Over/Under 0.5 Hits (-215/+165)
  Jared Triolo has hit the Hits Over in 15 of his last 20 games (+7.45 Units / 22% ROI)