MLB Picks Today: Expert Predictions & Best Bets for Monday, July 27, inc. Yankees vs White Sox

The all-star break is in the rearview mirror and the 2026 Major League Baseball season continues on with a compelling slate of games on Monday. The 12-game card features a couple of intriguing matchups, including a matchup of Yankees vs White Sox at 7:40 pm ET. The action gets underway at 2:35 PM ET with Mariners vs Rangers. Other games today are Red Sox vs Athletics, Orioles vs Tigers and Phillies vs Marlins.

Let's break down my MLB best bets for Monday, July 27, while you can also find out our expert MLB picks for EVERY GAME today and throughout the entire 2026 campaign!

MLB best bet: New York Yankees F5 -0.5 over Chicago White Sox (-112)

Odds available at FanDuel Sportsbook at time of publishing. Playable to -120.

We have a battle between a couple of potential playoff teams in the American League on Monday, as the White Sox will take on the New York Yankees. It hasn't been an easy last few months for New York, but the Yankees will have a serious edge on the mound in this one -- which is part of why I'll be targeting them in the first 5 innings instead of a full game number. Max Fried gets the ball for the pinstripes, and the veteran left-hander can be trusted to produce against a White Sox lineup that has been extremely up-and-down over the last few weeks. New York has its own problems at the plate without Aaron Judge and Cody Bellinger in the lineup, but the Yankees are in a good position to succeed against Noah Schultz (6.07 ERA, bottom 11 percent barrel rate, whiff rate and xBA). Let's look for the Yankees to lead after the first 5 innings and avoid any potential bullpen drama.

Read our full Yankees vs White Sox prediction for today's MLB matchup

MLB best bet: Boston Red Sox -1.5 over Athletics (-105)

Odds available at DraftKings Sportsbook at time of publishing. Playable to -115.

No team has played better than the Red Sox over the last month, and Boston should keep the good vibes going against a depleted Athletics team on Monday, especially given the pitching matchup. Manager Chad Tracy's team has consistently produced for its starting pitchers over this extraordinary 17-2 run, and we should see more of the same against Athletics starter Jack Perkins (6.75 ERA) and a bullpen that ranks dead last in ERA (5.51). While the Red Sox lineup should produce plenty of runs in this game, Boston should hold that lead with Payton Tolle on the mound. Tolle holds a 3.31 ERA and his expected numbers (2.93 xERA, .206 xBA) suggest that even better things are coming for the left-hander. I'll back Boston to win by multiple runs.

Check out our full Red Sox vs Athletics prediction for today's MLB game