Pittsburgh Pirates @ Boston Red Sox Player Props, Picks and Predictions - 8/29/2025 7:10 PM EDT

We have your Pittsburgh Pirates @ Boston Red Sox prop betting and game preview needs covered as the Pittsburgh Pirates hit the road to face the Boston Red Sox.

Pittsburgh Pirates @ Boston Red Sox Pick

Best Moneyline Odds: Boston Red Sox -110 (Caesars) / Pittsburgh Pirates +100 (Fanduel).
Best Spread Odds: -
Best Total Odds: -

Game Info

Date: August 29, 2025
Time: 7:10 PM EDT
Location: Fenway Park, Boston, MA
TV: MLB Network

Pittsburgh Pirates @ Boston Red Sox Preview

The Boston Red Sox (75-60) are set to host the Pittsburgh Pirates (59-76) in what promises to be an intriguing interleague matchup at Fenway Park. The Red Sox enter this series on a high note, having swept the Baltimore Orioles in a four-game set and boasting an impressive 7-1 record over their last eight outings. Their offense has been clicking, scoring 36 runs in that span, with key contributions from players like Trevor Story, who recently became the only AL player with 20 home runs, 20 stolen bases, and 80 RBIs this season. Boston's strong home record of 41-25 further solidifies their position.

On the other side, the Pittsburgh Pirates are also playing some good baseball, with a 6-2 record in their last eight games, despite dropping their recent series finale against the St. Louis Cardinals. Their offense has also managed to put up 36 runs in the same eight-game stretch as Boston. The Pirates will send their ace, right-hander Paul Skenes (8-9, 2.07 ERA), to the mound. Skenes has been dominant this season, with a 0.94 WHIP and an impressive 10.1 K/9 rate over 161 innings. He is coming off his ninth scoreless start of the year, and his career ERA of 2.02 is the second-lowest through 50 starts in the live-ball era. The Red Sox will counter with top pitching prospect left-hander Payton Tolle, who will be making his highly anticipated MLB debut. Tolle has shown promise in the minors, with a 1-1 record and a 3.60 ERA across 15 innings in Triple-A, striking out 133 batters in just over 91 innings across all minor league levels this season. Fenway Park, known for being a batter-friendly venue, could play a role in this contest.

Historic Head-to-Head Stats and Analysis

Specific historic head-to-head game results between the Pittsburgh Pirates and Boston Red Sox were not available in the provided research.

Pick: Boston Red Sox Moneyline

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The Boston Red Sox are the pick in this matchup. While the Pittsburgh Pirates have been playing well recently and boast an ace in Paul Skenes, the Red Sox's overall team form and home-field advantage are compelling. Boston has been red-hot, winning seven of their last eight games, including a sweep of the Orioles, and they hold a strong 41-25 record at Fenway Park. The sharp money also appears to be leaning towards the Red Sox, with a 51.75% sharp win percentage on their moneyline. Although Payton Tolle is making his MLB debut for Boston, the Red Sox offense has been consistently producing, and their momentum at home should be enough to secure a victory against a Pirates team that has struggled on the road with a 20-46 record this season.

Top Player Prop Picks

Paul Skenes - Pitcher Strikeouts Over 6.5

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Paul Skenes has been a strikeout machine this season, boasting a 10.1 K/9 rate. He has consistently hit the over on his strikeout prop recently, going over the 6.5 line in 80% of his last five games and 60% of his last ten games. His season average for strikeouts is 6.7, aligning closely with this line. Given his dominant form and ability to rack up strikeouts, taking the over on 6.5 strikeouts for Skenes at odds of -125 (BetMGM) is a strong play.

Roman Anthony - Hits Over 0.5

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Boston Red Sox outfielder Roman Anthony has been in excellent hitting form. He has recorded over 0.5 hits in 80% of his last five games and 80% of his last ten games, demonstrating consistent plate appearances. His season average for hits is 1.05, well above the 0.5 line. Playing at home, where he has a 64.52% hit rate over 0.5 hits this season, further boosts his chances. Betting on Roman Anthony to get over 0.5 hits at odds of -185 (BetMGM) looks promising given his recent performance.

Jared Triolo - Hits Over 0.5

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Pittsburgh Pirates infielder Jared Triolo presents a good opportunity for the hits prop. He has been hitting well recently, going over 0.5 hits in 80% of his last five games and 80% of his last ten games. While his season hit rate is 48.75%, his recent form is very strong. Furthermore, Triolo has a favorable historical matchup against the Red Sox, hitting over 0.5 hits in 66.67% of his appearances against them in 2024. Considering his recent consistency and past success against this opponent, taking Jared Triolo to get over 0.5 hits at odds of -225 (ESPN BET) is a solid choice.