Caleb Wilfinger
The 2025 MLB season keeps rolling along following the all-star break, and Monday features a full slate of action for us to enjoy. I’m 52-31 on my MLB best bets this year and the Pickswise MLB handicapping team as a whole is 103-66-6 in this article series this season, including being on a 25-10 run right now.
Let’s keep it going as we get into today’s top picks on Monday, July 21. You can also find out our MLB picks for EVERY GAME today.
MLB best bet: Philadelphia Phillies F5 -0.5 over Boston Red Sox (-140)
Odds available at BetMGM Sportsbook at time of publishing. Playable to -150.
For my first MLB best bet for today, we’ll focus on an interleague matchup between the Red Sox and Phillies. Boston has been playing some incredible baseball over the last few weeks, but they’ll be operating at a disadvantage on Monday, specifically when it comes to the pitching matchup.
It all starts with on the mound for Philadelphia, as Zack Wheeler — one of the best pitchers in the game — holds a 2.36 ERA through 19 appearances, while ranking inside the top 10% of all qualified starters in xERA, xBA, hard-hit rate and strikeout rate (Baseball Savant). On the other side, Boston is countering with Walker Buehler, whose metrics (6.12 xERA, bottom 10% whiff rate, 1.56 WHIP) clearly indicate that he’s one of the lesser starting pitchers in the American League. That doesn’t bode well against a Phillies lineup that is a top 10 unit in baseball in a myriad of metrics. Let’s back the Phillies to get back on track by leading after 5 innings on Monday.
MLB best bet: Cleveland Guardians F5 -0.5 over Baltimore Orioles (-135)
Odds available at DraftKings Sportsbook at time of publishing. Playable to -150.
Our 2nd MLB best bet today takes us to Cleveland, where the Orioles are set to take on the Guardians. Cleveland is going with Tanner Bibee on the mound, and the right-hander’s expected metrics (3.64 xERA) suggest that he’s due for some positive regression in this series opener. Conversely, Baltimore will counter with Tomoyuki Sugano, and his extremely poor expected metrics (5.80 xERA, .305 xBA, bottom 3% strikeout rate) appear to be catching up with him based on his recent outings, as he’s allowed 16 runs over his last 15.2 innings pitched. Cleveland doesn’t have one of the strongest offenses in baseball by any means, but I’ll still take the better starter and better overall team to be leading after 5 innings on Monday.
