Pittsburgh Pirates

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

Fenway ParkMLBN, NESN, SNPT
Pirates
59-76
Pirates
Today
Red Sox
75-60
Red Sox
Boston Red Sox

Pirates vs Red Sox Pickswise Expert Predictions

Pittsburgh Pirates
Money Line Pick
PIT Pirates Win(-110)

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.

If you’re looking for a new sportsbook for the football season, we recommend checking out Fanatics Sportsbook. New users can get up to $100 back in FanCash EVERY GAMEDAY UNTIL OCTOBER if their football bet loses! Join Fanatics Sportsbook, where you can bet on our Pirates vs Red Sox predictions.

Boston Red Sox
Photo of Jason Fragomeni

Jason Fragomeni

Jason Fragomeni is a MLB sports writer for Pickwise who lives in New York and is a huge fan of the New York Yankees and New York Giants. Jason is a data/statistic fanatic and he’s learned how to apply statistical analyses into the sports betting world. Jason uses data every day to help him determine what picks have the greatest probability of winning, which has helped him when it comes time to make a wager. Jason has been in the sports industry for over 10 years now, and has a wealth of knowledge surrounding sports and is a sports bettor by hobby.
Read more about Jason Fragomeni
Pickswise
*
By signing up you agree to our terms and privacy policy