NFL Previews 
MLB Previews 
NBA Previews 
NHL Previews 
Soccer Previews 
Prediction 
Odds 
Last Recap 
Game Picks 
Top Handicapper 
Red Sox vs Pirates Picks and Predictions — August 30, 2025
The Boston Red Sox turn to top pitching prospect Payton Tolle on Friday night as they open a three-game series at Fenway Park against Paul Skenes and the Pittsburgh Pirates. Tolle, the 22-year-old lefty drafted out of TCU in 2024, makes his highly anticipated MLB debut against one of the game’s most dominant young arms.
Exclusive Access: Ultimate MLB HQ
Don’t watch—win with us.
Boston enters the series riding high after an 8-0 road trip capped with a sweep in Baltimore, climbing within 3.5 games of first place in the AL East. Pittsburgh has won seven of its last 10 but dropped Thursday’s finale in St. Louis. For a broader view of both teams’ form, track their recent performances in the MLB game results.
Want expert MLB betting advice tonight? Check the latest picks →
Boston Can Win If…
Payton Tolle keeps his nerves in check and delivers a solid first outing. The rookie struck out 133 in just over 91 innings in the minors this season and showed elite command, but the spotlight will be intense against Skenes.
Trevor Story leads the way offensively, becoming the only AL player with 20 homers, 20 steals, and 80 RBI this year. The Red Sox are an astounding 20-1 when he goes deep. If Story and Rob Refsnyder (who homered Thursday in his return) stay hot, Boston can support its young pitcher.
“Just a good player playing elite baseball,” manager Alex Cora said of Story. “All the work he put in last year is paying off.”
Pittsburgh Can Win If…
Paul Skenes stays in rhythm and the Pirates get timely hitting from their supporting cast. The reigning Rookie of the Year owns a 2.07 ERA and is coming off his ninth scoreless start of the year. His career ERA (2.02) is the second-lowest through 50 starts in the live-ball era.
“He’s always in control, which is really impressive,” manager Don Kelly said.
Offensively, Pittsburgh needs more from Oneil Cruz, who leads the NL with 35 steals but is 0-for-9 since returning from the IL. If Cruz finds his swing, the Pirates can pressure Boston’s debut arm early.
Key MLB Betting Trends
| Category | Red Sox | Pirates |
|---|---|---|
| Record | 74-59 | 66-67 |
| Last 10 Games | 8-2 | 7-3 |
| Runs Per Game | 4.9 | 4.4 |
| Team ERA | 3.92 | 3.75 |
| Season Series 2024 | N/A | N/A |
The Lean
Pick: Pirates -125 (Skenes)
Projected Final Score: Pirates 4, Red Sox 2
This game is all about the pitching duel. Skenes is already an ace, while Tolle is just beginning his journey. Boston’s lineup is capable, but debut jitters against a Cy Young candidate tilt the edge toward Pittsburgh. Expect a low-scoring battle where Skenes proves too much.
Stay ahead of every debut and contender matchup with our MLB betting previews page.
Chasing division titles or playoff spots? Don’t miss your edge. Get daily MLB best bets here →
