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Boston Red Sox vs. Pittsburgh Pirates prediction, pick for Friday 8/29/25

Boston Red Sox vs. Pittsburgh Pirates prediction, pick for Friday 8/29/25

Published:

By: Landon Silinsky

This is the first game of a three-game series in Boston between the Red Sox and visiting Pittsburgh Pirates.

Paul Skenes is scheduled to pitch for Pittsburgh, while Payton Tolle is slated to start for Boston.


Red Sox vs. Pirates prediction, preview

What more can you say about Paul Skenes at this point? The second-year phenom is the clear frontrunner for the NL Cy Young Award and continues to put together a truly ridiculous season. Skenes leads all of MLB with a 2.07 ERA and boasts a microscopic 0.94 WHIP, along with 181 strikeouts over 161 innings. The only thing holding him back is a lack of run support—his record sits at just 8-9 despite his dominance.

He’s coming off yet another gem in his last outing, tossing seven shutout innings against the Rockies while allowing just three hits, no walks, and striking out seven. It was the 10th time in 27 starts this season that Skenes didn’t allow a single run. He’ll face a much tougher test Friday night at Fenway Park, but there’s no reason not to expect another dominant showing.

On the other side, the Red Sox will be calling up left-hander Payton Tolle from Triple-A to make his MLB debut. Tolle has been outstanding for Worcester, posting a 3.04 ERA and 0.99 WHIP with 133 strikeouts in just 91.2 innings.

Despite having to square off with Skenes, Tolle couldn’t ask for a much softer landing in his debut—the Pirates rank dead last in MLB in runs scored, slugging percentage, and OPS.

Boston enters the game riding a four-game win streak and has won seven of its last 10. Pittsburgh is also playing solid baseball, winning seven of 10 as well—though some of those wins did come against the Rockies and Cardinals.

Red Sox vs. Pirates pick, best bet

Even with the Red Sox’s high-powered offense, it’s hard to see Skenes giving up much in this game. The real question is how well Tolle handles his MLB debut. Nerves aside, he’s facing a Pirates lineup that simply can’t produce runs. This feels like a classic low-scoring affair—something like a 2-1 game with Boston scratching across a late run against the Pirates’ bullpen. I’ll take the under here.

Best Bet: Under 8 Runs (-115)

Landon is part-time editor and full-time DFS/Best Ball player. When he’s not buried in Strokes Gained Data or NFL target shares, he enjoys spending time with his mini poodle William.
Disclaimer

I am a promoter at DraftKings and am also an avid fan and customer (my username is Lan1228) and may sometimes play on my personal account in the games that I offer advice on. Although I have expressed my personal view on the games and strategies above, they do not necessarily reflect the view(s) of DraftKings and do not constitute a representation that any particular strategy will guarantee success. All customers should use their own skill and judgment in building lineups. I may also deploy different players and strategies than what I recommend above. I am not an employee of DraftKings and do not have access to any non-public information.