The Pittsburgh Pirates and Boston Red Sox begin a three-game set at Fenway Park on Friday night.
Top pitching prospect Payton Tolle will make his MLB debut for Boston, while Pittsburgh counters with NL Cy Young favorite Paul Skenes which is why my Pirates vs Red Sox predictions are betting the Under.
Here are my best free MLB picks for this interleague clash on August 29.
Pirates vs Red Sox prediction
Pirates vs Red Sox best bet: Under 8 (-115)
Payton Tolle entered this season as the No. 28 overall prospect in baseball and the No. 3-ranked left-handed pitcher. After logging just 42 innings at the Double-A and Triple-A levels (2.34 ERA, 0.79 WHIP), he has gotten the call-up to the Boston Red Sox.
The Red Sox have called up Payton Tolle! per.@Ken_Rosenthal
— Running From The OPS (@OPS_BASEBALL) August 28, 2025
The 6'6", 250-pound lefty generates nearly 7.5 feet of extension and features some of the best stuff in MiLB, with a deep five-pitch mix. In 15.0 IP at AAA, he posted a 28.8% K% and a 69.9% strike rate. pic.twitter.com/gu6dOIxiKe
The southpaw couldn't ask for an easier matchup than the Pittsburgh Pirates, who are last in last in the majors in runs per game (3.59) and OPS (.657). The Buccos have been even worse on the road, where they plate just 3.23 runs per game with an OPS of .616.
While Pittsburgh won't score many runs, they also won't allow many with ace Paul Skenes on the hill. The super sophomore leads the majors in ERA (2.07) and WAR (6.2) while ranking third in WHIP (0.94).
The Red Sox are productive at the plate but have seen a drop-off this month. They are 20th in the majors in slugging percentage in August (.395). With both sides cashing Under tickets at a high rate, bet the Under 8 tonight.
Pirates vs Red Sox same-game parlay (SGP)
Skenes is sixth in the majors in strikeouts (161) and has fanned 8+ batters in four of his last six starts. Boston is 22nd in the majors in strikeout rate while ranking 25th in whiff rate.
Pham is slugging just .329 against lefties this year. He's batting .233 this month and will have a tough time against Tolle and a Boston bullpen that ranks third in the majors in ERA (3.37).
Pirates vs Red Sox odds
- Moneyline: Pittsburgh -110 | Boston -110
- Run line: Pittsburgh -1.5 (+155) | Boston +1.5 (-185)
- Over/Under: Over 8 (-105) | Under 8 (-115)
Pirates vs Red Sox trend
The Pirates are 38-25-3 (60.3%) to the Under on the road this year. Find more MLB betting trends for Pirates vs. Red Sox.
How to watch Pirates vs Red Sox and game info
| Location | Fenway Park, Boston, MA |
| Date | Friday, August 29, 2025 |
| First pitch | 7:10 p.m. ET |
| TV | MLB Network |
| Pirates starting pitcher | Paul Skenes (8-9, 2.07 ERA) |
| Red Sox starting pitcher | Payton Tolle (0-0, 0.00 ERA) |
Pirates vs Red Sox latest injuries
Pirates vs Red Sox weather
Odds are correct at the time of publishing and are subject to change.
Not intended for use in MA.
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