Pittsburgh (59-76) vs Boston (75-60)
August 29, 2025 at 07:10 PM EDT
The Line: Betting Odds: Boston -110 — Over/Under: +8
The Pittsburgh Pirates and the Boston Red Sox meet Friday in MLB action from Fenway Park. We will look at this from a betting perspective and determine the best bets for this game. Here’s a Pittsburgh Pirates vs. Boston Red Sox prediction.
Starting Pitching Matchup
The Pittsburgh Pirates will send out Paul Skenes for the start here and Skenes is 8-9 with a 2.07 ERA and 181 strikeouts this season. This will be Skenes’ first career start against the Red Sox. The Boston Red Sox did not have a starter announced at the time that this article was posted.
Pittsburgh Pirates Recap
The Pittsburgh Pirates come into this game looking to rebound from a 4-1 loss at the hands of the St. Louis Cardinals to sit at 59-76 on the year. After this series, the Pirates will head on the road for a series against the Los Angeles Dodgers.
Pirates Win 7 Of Last 10 Despite Thursday’s Loss
Bryan Reynolds has 122 hits with 34 doubles, 14 home runs and 66 RBIs while also posting 148 strikeouts so far this season. Oneil Cruz has posted a team-high 18 home runs and 52 RBIs with 35 stolen bases while Isiah Kiner-Falefa has 105 hits with 20 doubles and 15 stolen bases. Cruz also has a team-high 149 strikeouts as well this season. Tommy Pham has 14 doubles and Andrew McCutchen has 96 hits with 19 doubles as well this season.
Why the Pittsburgh Pirates will win
- The Red Sox have lost each of their last six night games against NL Central opponents following a road win.
- The road team has won each of the last six games between the Pirates and Red Sox.
- The Red Sox have failed to cover the run line in each of their last 12 Friday night home games against National League opponents.
- The road team has covered the run line in each of the last six games between the Pirates and Red Sox.
Pittsburgh Pirates Player Prop Facts
- Bryan Reynolds has hit at least one home run in two of the Pirates’ last three road games against the Red Sox.
- Bryan Reynolds has recorded at least one Double in five of the Pirates’ last six night games.
- Jared Triolo has recorded at least one hit in 12 of his last 13 appearances in night games against AL teams that held a winning record.
- Paul Skenes ranks 1st amongst qualified players for Earned Run Average (2.07) this season.
Boston Red Sox Recap
The Boston Red Sox come into this game looking to add on to their sweep over the Baltimore Orioles thanks to a 3-2 win in Thursday’s series finale to sit at 75-60 this season. After this series, the Red Sox will take on the Cleveland Guardians in a series at home.
Red Sox Win 4 Straight and 7 Of Their Last 8
Alex Bregman has 98 hits including 24 doubles along with 16 home runs and 53 RBIs this season. Trevor Story’s added 130 hits with 22 home runs, 84 RBIs and 23 stolen bases while Jarren Duran has 134 hits with 34 doubles, 12 triples, 13 home runs, 73 RBIs and a team-high 22 stolen bases. Roman Anthony’s added 69 hits with 18 doubles, 7 home runs and 29 RBIs while Wilyer Abreu has 22 home runs with 69 RBIs and 6 stolen bases and Ceddanne Rafaela has 15 homers, 29 doubles, 3 triples, 55 RBIs and 19 stolen bases this season.
Why the Boston Red Sox will win
- The Red Sox have won nine of their last 10 games against National League opponents that held a losing record.
- The Pirates have lost eight of their last nine road games against American League opponents.
- The Pirates have failed to cover the run line in 14 of their last 16 night games against AL East opponents.
- The Red Sox have covered the run line in seven of their last eight home games against National League opponents after playing the previous day.
Boston Red Sox Player Prop Facts
- Trevor Story has recorded a Double in each of the Red Sox’s last four games against NL Central opponents at Fenway Park.
- Triston Casas has recorded at least one hit in each of his last 11 appearances against NL opponents that held a losing record.
- Triston Casas has hit a home run in each of his last three appearances against NL Central opponents that held a losing record.
Total Runs Facts
- Each of the Red Sox’s last four games have gone UNDER the total runs line.
- Four of the Pirates’ last five road games against American League opponents have gone UNDER the total runs line.
Pittsburgh Pirates vs. Boston Red Sox Prediction
I’m on the under here. Skenes has been rock solid in his starts this year with a sub-2.00 ERA as we’re entering September, but the reason he has a losing record is that he often doesn’t get run support from his bats. We could potentially see the Major League debut of Payton Tolle here, a top lefty in Boston’s system and if Tolle goes here, the Pirates really struggle against lefties. Either way, I see this game coming in under the number so give me the under here.