It might be a getaway day for many teams, but there are still some intriguing matchups on the MLB schedule tonight. After looking through every game using the AI Model, I’ve found some upsets we’ll want to target for tonight’s underdog picks in the MLB.
Boston Red Sox vs. New York Yankees
Thursday, August 21, 2025 – 7:15 PM EDT at Yankee Stadium
The Boston Red Sox are expected to lose to the Yankees by only .3 runs. Yet, the Red Sox are +122 on the moneyline. The AI Model thinks the Red Sox can keep it close. Therefore, at +122, Boston is a go tonight.
Luis Gil Is Too Wild
The Yankees will pitch Luis Gil tonight. He’s a righty who has walked more than 13% of his last 61 batters.
Plus, he’s induced just 28.2% of grounders during that time and has allowed a .360 wOBA. Gil won’t have it easy against a Red Sox lineup that has a ton of power and patience.
He’ll go up against Lucas Giolito, who has not been good against lefties. Yet, he’s done well against righties, and the righties in the New York lineup have typically performed better than lefties over the last 30 days.
I’d much rather take Lucas Giolito as an underdog in a rivalry game. Side with the AI Model and take the Red Sox at +122 at Caesars Sportsbook.
MLB Pick: Red Sox ML (+122) at Caesars
Houston Astros vs. Baltimore Orioles
Thursday, August 21, 2025 – 7:15 PM EDT at Oriole Park at Camden Yards
The AI Model predicts the Houston Astros will escape the Baltimore Orioles on the road, 4.4-4.3. However, the Astros are -105 at BetMGM and slight underdogs in this game.
Will Young Be Mentally Prepared?
Fresh off a near-perfect game, Brandon Young will get the start for the Orioles. Typically, in these situations, the player who pitched very well in the previous start is overwhelmed in his next start.
Look for that to be the case tonight against the Astros’ lineup that doesn’t strike out often against righties.
Conversely, it’ll be Jason Alexander for the Astros. Alexander has limited his last 116 batters to a .152 ISO and wOBA of .284 thanks to a high ground ball rate and low fly ball rate. He won’t add a bunch of strikeouts, but certainly won’t let up much power. He’s facing an Orioles lineup that has collectively hit a .140 ISO against righties over the last month.
Take the Astros as slight underdogs.
MLB Pick: Astros ML (-104) at BetMGM
St. Louis Cardinals vs. Tampa Bay Rays
Thursday, August 21, 2025 – 7:35 PM EDT at George M. Steinbrenner Field
The AI Model believes the Cardinals will add a nearly one-run win over the Rays tonight. Meanwhile, you can find the Cardinals at -1.5 at +145. There’s so much value in using the Cardinals on the run line here.
Sonny Gray Will Be Fine
The St. Louis Cardinals will send out Sonny Gray for tonight’s game against the Rays. The veteran righty has struck out 25.6% of batters over the last month. He’s also walked just 4% of batters during that stretch.
But despite those incredible numbers, he’s still allowed a .227 ISO and wOBA of .359 to his last 125 batters. That’s not ideal, but he’s still issued 46% of grounders and has limited line drives to below 22% over the same stretch.
Luck will reach his side eventually. Plus, he’s facing a Rays’ lineup that has hit a .147 ISO and wOBA of .304 against righties over the last month.
That said, the Cardinals haven’t been much better against righties over the last 30 days. Still, they’re facing Joe Boyle, who has had command issues. He’s also allowed a .333 ISO and wOBA of .402 over the last month. I’ll back the Cardinals at -1.5.
MLB Pick: Cardinals -1.5 (+145) at BetMGM
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