MLB Bets Today: Same-Game Parlays and Props for Wednesday, August 27
2025 Betting Record: 36-36-2 (-1.88 units)
2025 Player Props Betting Record: 19-16 (+1.06 units)
I'm focusing on a pair of battles in AL venues Wednesday where the pitching matchups definitely seem to tilt toward one team's favor.
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Best MLB Bets Today
Boston Red Sox at Baltimore Orioles Best Bets
The Red Sox are solid road favorites for this AL East evening tilt, and the pitching matchup is playing a sizable role. Baltimore will go with Dietrich Enns as an opener before turning to Roansy Contreras, who's being called up from Triple-A Norfolk, for bulk-relief work.
Contreras has certainly had flashes of success at the big-league level, and he's put together a solid body of work at Norfolk this season with a 7-3 record, 3.73 ERA and 1.30 WHIP. However, he holds a 4.72 ERA and 1.39 WHIP across his 90 big-league appearances (33 starts), and he's averaged just under four walks per nine innings in that span as well.
The Red Sox haven't been at their best on the road, but they've got their eyes set on the postseason and have dominated the season series with Baltimore thus far to the tune of a 5-1 advantage. Boston starter Brayan Bello had a hiccup against the Padres three starts ago, but he's otherwise allowed three earned runs or less in every start dating all the way back to May 23.
Bello recorded seven strikeouts of these same O's over just four innings in that outing, and he has 15 Ks of current Baltimore hitters in 52 career encounters. He's also held them to a collective .229 average and .288 OBP over that sample. The Orioles also have a 25.3% K%, .203 average, .282 wOBA and -9.6 wRAA against righties at home in August.
Given the factors cited, I'm in the camp of an SGP that banks on a Red Sox lead after five innings and Bello getting to at least five strikeouts for the 10th time this season. Then, with Bregman sporting a .283 average, .895 OPS and .379 wOBA against right-handed pitching outside Fenway – as well as an .859 career OPS at Camden Yards and an average of 2.3 hits+runs+RBI this season – I like his chances of getting to at least a combined two hits + runs + RBIs.
MLB Picks for Red Sox at Orioles
- SGP: Red Sox moneyline-F5 and Brayan Bello Over 4.5 Strikeouts (+170 on BetMGM Sportsbook) for 1 Unit
- Alex Bregman Over 1.5 Hits + Runs + RBI (-135 on BetMGM Sportsbook)
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Colorado Rockies at Houston Astros Best Bets
An even bigger pitching mismatch awaits in this interleague matchup at Minute Maid Field, where Chase Dollander will toe the rubber for the visitors against Framber Valdez.
Dollander has been much better on the road than at Coors, so there's certainly a chance for him to piece together a solid performance. However, he's still allowing a 4.0 BB/9 and 1.3 HR/9 when traveling, which is more than enough to get him into trouble against a talented Astros lineup, even when taking Houston's troubles generating offense at home of late into account.
The return of Yordan Alvarez after a long layoff will naturally help the Astros' run production over time, and a matchup against an inexperienced Dollander and a bullpen that can certainly have its fair share of breakdowns as well could certainly set Houston up for its 39th home victory.
Valdez has also posted a 9.8 K/9 at home alongside a 1.85 ERA and 1.09 WHIP over 77.2 innings. The Rockies have been better against lefties on the road lately but have a 25.4% K%, .278 wOBA and -15.4 wRAA in that split for the season. Therefore, I'm backing an SGP that banks on a Houston win and Valdez getting to at least seven strikeouts for the 12th time this season.
Meanwhile, a prop based on the talented Pena, who's averaging 1.9 total bases per game and has a .353 average and .946 OPS at home, getting to at least two total bases is also in play in a game the Astros are projected for a robust 5.3 runs.
MLB Picks for Rockies at Astros
- SGP: Astros moneyline and Framber Valdez Over 6.5 Strikeouts (+125 on BetMGM Sportsbook) for 1 Unit
- Jeremy Pena Over 1.5 Total Bases (+105 on BetMGM Sportsbook) for 1 Unit
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MLB Picks Recap
- SGP: Red Sox moneyline-F5 and Brayan Bello Over 4.5 Strikeouts (+170 on BetMGM Sportsbook) for 1 Unit
- Alex Bregman Over 1.5 Hits + Runs + RBI (-135 on BetMGM Sportsbook)
- SGP: Astros moneyline and Framber Valdez Over 6.5 Strikeouts (+125 on BetMGM Sportsbook) for 1 Unit
- Jeremy Pena Over 1.5 Total Bases (+105 on BetMGM Sportsbook) for 1 Unit
