The Pittsburgh Pirates and Boston Red Sox begin a three-game series tonight at Fenway Park.

Boston enters the matchup riding a four-game winning streak, sitting 3.5 games behind the division-leading Toronto Blue Jays in the AL East.

The wild-card race is even tighter: the Red Sox trail the New York Yankees by just half a game for the top spot, while maintaining a comfortable five-game cushion over the Kansas City Royals, who are just outside the playoff picture.

On paper, this series looks like an opportunity to gain ground. The Pirates sit at the bottom of the NL Central with a 59–76 record. But they’ve quietly won seven of their last 10 and bring ace Paul Skenes to the mound tonight.

Skenes is having a stellar second year, posting a 2.07 ERA, though with an 8–9 record. His numbers suffer only because of the Pirates’ lack of run support. The team ranks dead last in MLB in both home runs and runs scored. Still, opponents are well aware he can shut down any lineup.

Boston sends rookie Payton Tolle to the mound. Just 22 years old and drafted in the second round out of TCU in 2024, Tolle has rocketed through the minors this season, making 11 starts at High-A, six at Double-A, and three at Triple-A.

At Worcester, he posted a 1–1 record with a 3.60 ERA and 17 strikeouts in 15 innings. He now takes the roster spot vacated by Walker Buehler, who was designated for assignment after a move to the bullpen failed to stick.

Tolle’s debut is a wild card. He could surprise with poise, or the Pirates might pounce on the inexperience.

What’s more certain is that Skenes will deliver a strong start. The question is whether Pittsburgh’s bats can do enough against Boston’s rookie arm. Expect a low-scoring contest unless Tolle falters early.

Prediction

Skenes gives Pittsburgh a chance, but the Red Sox lineup does enough damage on the Pittsburgh bullpen to support Tolle in his debut. Expect a tight pitchers’ duel.

Prediction: Red Sox 3, Pirates 2

Starting Lineups

Pittsburgh Pirates

1. Jared Triolo – SS

2. Nick Gonzales – 2B

3. Bryan Reynolds – RF

4. Tommy Pham – LF

5. Andrew McCutchen – DH

6. Alexander Canario – CF

7. Henry Davis – C

8. Liover Peguero – 1B

9. Isiah Kiner-Falefa – 3B

Starting Pitcher: Paul Skenes (RHP) — 8–9, 2.07 ERA

Boston Red Sox

1. Roman Anthony – RF

2. Alex Bregman – 3B

3. Jarren Duran – LF

4. Trevor Story – SS

5. Masataka Yoshida – DH

6. Romy Gonzalez – 1B

7. Nick Sogard – 2B

8. Ceddanne Rafaela – CF

9. Connor Wong – C

Starting Pitcher: Payton Tolle (LHP) — MLB Debut

How to Watch Pirates vs. Red Sox

First pitch for tonight’s Pirates–Red Sox game is scheduled for 7:10 PM Eastern at Fenway Park in Boston.

The game will air on NESN in New England, SportsNet Pittsburgh for Pirates fans, and will stream nationally on MLB Network (out-of-market only).

Pittsburgh Pirates vs. Boston Red Sox

Date: Friday, August 29, 2025

First Pitch: 7:10 PM Eastern

Venue: Fenway Park, Boston, MA

TV: NESN (Red Sox), SportsNet Pittsburgh (Pirates), MLB Network (out-of-market)

Streaming: MLB.TV