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Boston Red Sox at Baltimore Orioles prediction, pick for Wednesday 8/27/25

Boston Red Sox at Baltimore Orioles prediction, pick for Wednesday 8/27/25

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By: Garion Thorne

It’s been a strange season for the Red Sox. At times back in April, May and June, it felt like Boston could miss the playoffs entirely — especially after the club decided to trade away perennial All-Star Rafael Devers. However, there’s also been moments of great optimism, whether that was an eight-game winning streak against the hated Yankees or the arrival of super prospect Roman Anthony.

As it stands on Wednesday, Boston is just four games back of Toronto for the AL East crown and the team will look to win the third contest of a four-game set against the Orioles. Seems like pretty good times!

Let’s preview this divisional matchup with the help of some odds and lines on the DraftKings Sportsbook.

Red Sox vs. Orioles prediction, preview

It’s not that people weren’t aware of Brayan Bello prior to last Friday’s performance against the Yankees, but I think it’s safe to say that that outing officially put the 26-year-old on the map. Bello tossed seven scoreless innings versus New York, giving up just three hits and a walk in the Bronx. It was the continuation of what we’ve been seeing for two-and-a-half months from the RHP, as Bello sports a 2.50 ERA and a 1.02 WHIP dating all the way back to June 15. That’s a span of 13 starts and 82.2 innings, too. We’re no longer dealing with small samples.

Wednesday feels like it should be a good matchup for Bello to keep riding high. The Orioles have struggled to score runs since trading away several veteran bats at the deadline, while re-losing Adley Rutschman (oblique) and Jordan Westburg (ankle) to the IL has not helped, either. Since the start of August, Baltimore ranks 26th in batting average (.220) and 27th in wRC+ (82). If you need an example of the Orioles’ recent woes, look no further than last night’s 5-0 loss. Lucas Giolito has been good lately, but not that good.

Also working in Boston’s favor? Baltimore will be utilizing a bullpen game, with Dietrich Enns opening and making his first “start” with the Orioles. Enns does have some experience as a starter, even throwing 83 pitches as recently as July 3 in Washington, back when the 34-year-old lefty was still a member of the Tigers. Enns will likely stay on the mound for as long as he’s effective, which could be a while even in a very difficult matchup. An absurd .388 opponent BABIP has inflated Enns’ ERA in 2025, but the journeyman does have a 3.09 FIP across 29.0 innings with 32 strikeouts. He’s no slouch.

Red Sox vs. Orioles pick, best bet

Best Bet: Red Sox -1.5 (+109)

Boston’s won five of its last six games and it should be able to best a bullpen game from an Orioles team that traded away several RPs at the deadline.

Strong Lean: Brayan Bello 5+ Strikeouts (-135)

Baltimore owns the league’s fifth-highest strikeout rate in August (24.6%).

Garion is a Toronto-based writer who has been playing fantasy sports since elementary school. With a particular affinity for advanced statistics and sabermetrics, he’s been covering DFS Baseball, Football and Basketball for DraftKings dating back to 2018. Prior to that, Garion’s work could be found at FNTSY, SportsGrid, HoopsHype, The New York Daily News and Sportsnet.ca. Still, he is a Dolphins fan, so his decision-making can be questioned from time-to-time.
Disclaimer

All views expressed are my own. I am an employee of DraftKings and am ineligible to play in public DFS or DKSB contests.