Orioles vs. Red Sox Prediction, Odds, Probable Pitchers and Prop Bets for Monday, Aug. 18

Can the Orioles pull off an upset on Monday night?

Baltimore Orioles starting pitcher Trevor Rogers is a solid prop target on Monday. / Dale Zanine-Imagn Images

The Baltimore Orioles are extreme long shots to make the playoffs (less than a 1 percent chance at FanGraphs) heading into their early-week series with the Boston Red Sox, who have seen their playoff odds slip over the last week. 

Boston is still in second in the AL East and holds the top wild card spot, but it is just a half-game ahead of the New York Yankees (the No. 3 wild card) entering Monday’s action. 

Dustin May (4.67 ERA) is on the mound for the third time in a Boston uniform in Monday’s series opener. May is coming off six shutout innings in a win over Houston, and he’s looking to carry that momentum into a home start against Baltimore.

The Orioles will have a former All-Star in lefty Trevor Rogers on the mound in this game, and he’s been great in 2025, posting a 1.43 ERA and a 3.05 xERA in 11 outings. Can Rogers keep his strong 2025 going against a likely playoff team in the AL?

Here’s a breakdown of the odds, players to bet on in the prop market, and my prediction with Boston set as a slight favorite at many of the best betting sites. 

Orioles vs. Red Sox Odds, Run Line and Total

Odds via DraftKings Sportsbook

Run Line

• Orioles +1.5 (-205)
• Red Sox -1.5 (+167)

Moneyline

• Orioles: +102
• Red Sox: -124

Total

• 8 (Over -115/Under -106)

Orioles vs. Red Sox Probable Pitchers

• Baltimore: Trevor Rogers (5-2, 1.43 ERA)
• Boston: Dustin May (7-8, 4.67 ERA)

Orioles vs. Red Sox How to Watch

• Date: Monday, Aug. 18
• Time: 7:10 p.m. EST
• Venue: Fenway Park
• How to Watch (TV): NESN, MASN
• Orioles record: 57-67
• Red Sox record: 68-57

Orioles vs. Red Sox Best MLB Prop Bets

Orioles Best MLB Prop Bet

• Trevor Rogers UNDER 5.5 Hits Allowed (-135)

Through 11 outings this season, Rogers has allowed six or more hits just one time, posting a WHIP of 0.81.

This is a tough matchup against a Boston offense that is No. 3 in MLB in batting average against left-handed pitching, but Rogers held the Sox to just two hits in 6.1 innings earlier this season.

The lefty has allowed four or fewer hits in eight of his starts, and I think he’s undervalued a bit at this number on Monday night. Overall, this season, Rogers has held opponents to an expected batting average of .232. 

Orioles vs. Red Sox Prediction and Pick

Will we see an upset in this AL East battle?

On Monday morning, I shared in SI Betting’s MLB best bets column – Walk-Off Wagers – why Rogers may be the pitcher to back tonight: 

Lefty Trevor Rogers has been a revelation for the struggling Baltimore Orioles this season, as he’s posted a 1.43 ERA in 11 outings while leading the O’s to an 8-3 record.

He’ll take on the Boston Red Sox and Dustin May (4.67 ERA) on Monday, as May attempts to build on a strong outing (six innings, five hits, no runs) in his last start against Houston. 

While May did turn things around in his second outing for Boston, he’s struggled a bit overall this season, posting a 1.35 WHIP and an expected ERA of 4.71, which ranks in the 19th percentile amongst MLB pitchers.

Boston has also slipped a bit as of late, winning just four of its last 10 games.

Baltimore is far from a playoff team, but it has rallied behind Rogers in the 2025 season. The lefty has an expected ERA of 3.05 (85th percentile), and he’s allowed three or fewer earned runs in every outing in 2025. 

I wouldn’t be shocked if he outduels May and leads the O’s to an upset win on Monday night. 

Pick: Orioles Moneyline (+102 at DraftKings)

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Odds refresh periodically and are subject to change.

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