Caleb Wilfinger
The 2nd half of the 2025 MLB season continues rolling along, and Friday features a full slate of action for us to enjoy. I’m 73-51-1 on my MLB best bets this year and the Pickswise MLB handicapping team as a whole is currently on a 12-3 run! Let’s keep it going as we get into today’s top MLB predictions on Friday, August 29. You can also find out our MLB picks for EVERY GAME today.
MLB best bet: Pittsburgh Pirates vs Boston Red Sox Under 8 (-110)
Odds available at DraftKings Sportsbook at time of publishing. Playable to -120.
For my first MLB best bet today, we’ll focus on this interleague matchup between the Pittsburgh Pirates and Boston Red Sox. Any time that Paul Skenes takes the mound for the Pirates, the under is going to immediately intrigue me. After all, Skenes is the top pitcher in the game for my money, posting a 2.07 ERA this season, to go along with top 10-15% marks in barrel rate, strikeout rate, expected batting average and walk rate (Baseball Savant). The Red Sox lineup has been getting it done situationally of late, but Boston has only put up 17 runs over its last 5 outings overall. Even on the road, Skenes should remain dominant in Friday’s contest.
As for the hosts, Boston is sending out its top pitching prospect Payton Tolle to make his MLB debut at Fenway Park. This will undoubtedly be a thrill for Tolle, and I expect him to see some success against a Pirates lineup that is dead last across baseball in slugging, OPS and runs scored this season. Ultimately, both pitchers should handle business regardless of result, so let’s back the under at the current number.
Find out our expert’s MLB YRFI/NRFI best bets for today
MLB best bet: Arizona Diamondbacks vs LA Dodgers F5 Under 4.5 (-110)
Odds available at DraftKings Sportsbook at time of publishing. Playable to -120.
For my 2nd MLB best bet on Friday, let’s roll with the under in the first 5 innings in Los Angeles between the Diamondbacks and Dodgers. After a very disappointing series against the Padres last weekend, Los Angeles seems to be back in good form and it all starts on the mound for the Dodgers in this one. Blake Snell (1.97 ERA, top 10% whiff rate) might not get all the spotlight on a team with this many stars, but the southpaw is still one of the best pitchers in the game, and has been rock solid since his return from injury on August 2. On the other side, Arizona starter Zac Gallen has pitched pretty well in August following a disastrous first half of the campaign, allowing just 10 runs over his last 5 outings, and he should at least hold his own for a couple of innings against a familiar foe. Let’s avoid any potential bullpen issues and back the under in the first 5 innings of this one.
