Pittsburgh Pirates vs Boston Red Sox Prediction – 8/29/2025
The Pittsburgh Pirates and Boston Red Sox will face one another in an interleague series opener on Friday night. Boston is at home and has had the better season so far. But they are at a massive starting pitching disadvantage in this game and will hope to overcome that to get a win here. Before this game begins, continue reading to get my Pirates vs Red Sox prediction for Friday’s matchup.
Our Pirates vs Red Sox Pick
- Pick: Pirates Moneyline
- Confidence: ★★★★☆
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Game Snapshot
- Matchup: Pittsburgh Pirates vs Boston Red Sox
- Date & Time: Friday, August 29, 2025, 7:10 p.m. ET
- Starting Pitchers: Paul Skenes (PIT) vs Payton Tolle (BOS)
- Stadium: Fenway Park, Boston, MA
- Broadcast: MLB.tv
Key Storylines
Pitching matchup
Paul Skenes has had a dominant sophomore season with an 8-9 record, 2.07 ERA, and a 0.94 WHIP. He has amassed 181 strikeouts across 161 innings and enters Friday as one of the top young arms in baseball. Boston will hand the ball to prospect Payton Tolle. He comes in fresh off a rise through the minors and impressive Triple-A work. Pittsburgh should have the pitching advantage here but the Red Sox will look to overcome that.
Key Players
- Pirates Bullpen: Skenes is likely to shut down the Red Sox early on. The question will be whether the bullpen of the Pirates can protect a lead or keep things competitive.
- Payton Tolle (BOS): Tolle is a highly ranked prospect making his first start. How he handles this moment mentally could be more important than his actual stuff on the mound.
Recent team streaks
- Boston has won four games in a row. They earned a four-game sweep over the Baltimore Orioles this week.
- The Pirates are 3-2 in their last five games and they split a four-game series with the Cardinals before coming to Boston.
Best Player Props
| Player | Prop |
|---|---|
| Trevor Story | Under 1.5 Total Bases |
| Paul Skenes | Over 7.5 Strikeouts |
| Payton Tolle | Under 4.5 Strikeouts |
Betting Trends & H2H
- This is the first head-to-head matchup between the Red Sox and Pirates to this point in the season.
- Pittsburgh is just 13-26 against interleague opponents so far this year.
- The Red Sox are 24-18 against opponents from the National League.
Pirates vs Red Sox Model Projection
Score Projection: Pirates 4 – Red Sox 3
Win Probability: Pirates 51%, Red Sox 49%
Final Thoughts
Tolle is an exciting prospect and one who could have a bright future in baseball ahead of him. But that doesn’t mean I expect him to show up and outperform Paul Skenes in his major league debut. Skenes should show Tolle what it’s like to be up against MLB-level talent here. I’ll go with the Pirates to win this game on the road in what is more or less a pick ’em contest.
