Pittsburgh Pirates vs Boston Red Sox Prediction, Odds and Picks for Today, 08/29/25

The red-hot Boston Red Sox will look to keep rolling as they welcome the Pittsburgh Pirates to town. Boston is reportedly calling up their top pitching prospect, Payton Tolle, to make his big-league debut tonight against the Pirates. During his time in the minors, Tolle went 3-5 with a 3.04 ERA in 20 games (18 starts) this year. He has 133 strikeouts and 23 walks in 91 ⅔ innings pitched. 

Facing Tolle and the Red Sox tonight will be Paul Skenes, who enters at 8-9 with a 2.07 ERA this season. Skenes has been terrific this season, though the rest of the Pirates haven’t provided much support. In their last 13 games, Pittsburgh is averaging just 4 runs per game, which happens to be slightly worse than the 4.2 runs per game for the Red Sox. This should be an exciting matchup to watch. However, with Tolle making his debut, it’s hard to know what to expect. Fortunately for him, the Pirates aren’t a power-hitting team, but at the end of the day, I trust Skenes in this matchup. The Red Sox have a much better bullpen than the Pirates, but I think the Pirates will do enough against Tolle early on and sneak out a win at Fenway.

Pirates vs Red Sox prediction: Pirates ML (-110) available at time of publishing. Playable at that number.

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