Caleb Wilfinger
The 2025 MLB season keeps rolling along, and Friday features a 9-game slate for us to enjoy. I’m 33-23 on my MLB best bets this year and the Pickswise MLB handicapping team as a whole is 76-56-6 in this article series this season. Let’s keep it going as we get into today’s top picks on Friday, June 27. You can also find out our MLB picks for EVERY GAME today, with our experts boasting a 35-13 record over the past 4 days!
MLB best bet: New York Yankees -1.5 over Athletics (-115)
Odds available at FanDuel Sportsbook at time of publishing. Playable to -125.
For my first MLB best bet for tonight, let’s head to New York for a matchup between the Athletics and Yankees. New York has struggled of late, particularly at the plate, but the Yankees’ bats did break out in their series-finale victory over the Reds on Wednesday. Now, Aaron Judge and company will have the good fortune of taking on Athletics starter Mitch Spence (4.72 xERA, .280 xBA), who is certainly due for some regression in his upcoming starts. On the other side, New York starter Will Warren has excellent stuff and is one of the premier strikeout pitchers in the game this season. Furthermore, Warren is also due for some positive regression (3.54 xERA), which should come at home against a middling Athletics lineup. Let’s take the Yankees on the run line.
Read our full Athletics vs Yankees prediction for tonight’s matchup
MLB best bet: Tampa Bay Rays F5 ML over Baltimore Orioles (-130)
Odds available at DraftKings Sportsbook at time of publishing. Playable to -135.
Our 2nd MLB best bet today takes us to Baltimore, where I’ll be targeting the Rays in the first 5 innings. Tampa Bay should be in a good position to succeed thanks to Ryan Pepiot getting the start in this one. The Rays’ starter has posted a 2.37 ERA over his last 10 starts, and he also hasn’t allowed more than 3 earned runs in any given start since April 15. He’ll be taking on a mediocre Orioles lineup that is just 23rd in batting average, slugging and OPS this season. Conversely, Baltimore will counter with Tomoyuki Sugano, and his poor expected metrics (4.97 xERA, .290 xBA, bottom 5% strikeout rate) appear to be catching up with him based on his recent outings, none of which have reached 5 innings. Ultimately, I’ll take the better starter and better overall team to at least be tied after 5 innings on Friday.
Read our full Rays vs Orioles prediction for today
