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Boston Red Sox vs Baltimore Orioles Odds, Picks & Predictions (May 27)

Sascha Paruk

by Sascha Paruk in MLB Baseball

Updated May 26, 2024 · 9:33 PM PDT

Baltimore Orioles left fielder Colton Cowser hitting a home run against the Boston Red Sox
Apr 11, 20024; Boston, Massachusetts, USA; Baltimore Orioles left fielder Colton Cowser (17) hits a home run against the Boston Red Sox during the fifth inning at Fenway Park. Mandatory Credit: Eric Canha-USA TODAY Sports
  • AL East rivals Boston and Baltimore start a three-game series on Monday, May 27
  • The Orioles are just two games back of the Yankees for first in the division while the Red Sox are 1.5 out of the final AL Wild Card
  • Below, see the Boston Red Sox vs Baltimore Orioles odds, picks, predictions, and starting pitchers for Monday’s game at Camden Yards

Looking for a season-best five-game win streak, the Baltimore Orioles (33-18, 17-10 home) welcome the Boston Red Sox (27-26, 16-11 away) to Camden Yards at 1:05 pm ET on Monday, May 27, for the first of a three-game series.

The matchup on the mound features two pitchers off to strong starts with Boston’s Cooper Criswell facing Baltimore’s Cole Irvin. Winners of four straight, Baltimore heads into Monday as a sizable moneyline favorite in the Red Sox vs Orioles odds.

Boston Red Sox vs Baltimore Orioles Odds

Team Moneyline Runline Total
Boston Red Sox (Criswell) +130 -1.5 (-155) O 8.5 (-125)
Baltimore Orioles (Irvin) -165 -1.5 (+130) U 8.5 (+105)

Baltimore is currently a -165 moneyline favorite with Boston at +130 to win straight-up in Monday’s MLB odds. The game total is sitting at 8.5. The Orioles have been the second-best over team in baseball this season (26-20-5 O/U) but Boston has hit the under at the second-highest rate (19-30-4 O/U).



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Odds as of May 27 at Caesars Sportsbook. Download the best MLB betting apps to wager on today’s games. 

The O’s are coming off a four-game sweep of the lowly Chicago White Sox, who are dead-last in the majors in both win percentage (.278) and run differential (-116). The Bo-Sox dropped two of three to the Milwaukee Brewers over the weekend but won last time out and are 5-2 in their last seven games.

Monday’s MLB public betting splits heavily skew towards the Orioles. Baltimore is getting 98% of moneyline handle and 86% of runline handle as of publication time. The public was also heavily back the over, with 81% of handle on over 8.5.

Boston vs Baltimore Starting Pitchers for May 27

Monday’s pitching matchup features two hurlers exceeding expectations in 2024. A product of the Rays’ vaunted player-development system, 27-year-old Cooper Criswell is excelling in his first season with the Red Sox. Criswell has a 2.86 ERA and 1.13 WHIP in eight appearances, and Boston is 6-1 straight-up in his seven starts.

Last time out, he went 5.1 innings against the Rays, allowing two runs on six hits with six strikeouts.

Not a single player on the Orioles has ever had an at-bat against Criswell.

Cooper Criswell vs Cole Irvin

2-1 Record 4-2
2.86 ERA 3.15
3.35 xERA 4.05
1.13 WHIP 1.09
23.9% SO% 16.4%

Baltimore will send Cole Irvin to the mound on Monday for his eighth start (and tenth appearance) of the season. Irvin is posting career-bests in ERA (3.15), xFIP (4.05), WHIP (1.09), HR/9 (0.79), and BB/9 (1.58) early in the season. Since allowing nine earned runs combined in his first two starts of the year, he’s allowed three or fewer in each of his last seven appearances. That said, his last start was one to forget: five runs (three earned) on six hits of just 3.1 innings against St Louis in a 5-4 loss.

Irvin’s history against the Boston lineup is not terribly encouraging, though it is a limited sample size. In 37 total at-bats, the Red Sox hitters are slashing .297/.333/.514 with two home runs (courtesy Martin Maldonado and Andrew Vaughn), two doubles, and seven RBI.

Red Sox vs Orioles Predictions

The Orioles swept the Red Sox when the teams met at Fenway back in early April, outscoring Boston 23-10 in the process. The O’s lineup ranks higher in almost every meaningful hitting category, including wOBA (.322 vs .315), wRC+ (111 vs 98), and slugging (.436 vs .404), and they strikeout considerably less (21.3% vs 25.4%).

Criswell’s start to the season has been a nice story, but this isn’t a pitcher with overpowering stuff. He doesn’t throw a traditional fastball, relying instead on a mix of his sinker (which tops out at about 90 mph), changeup, and slider. FanGraphs projects his strikeout percentage to drop from 23.9% to just 17.9% and his ERA to balloon from 2.86 to 4.73.

I expect the regression to start on Monday.

BOS vs BAL picks:

  • Orioles moneyline (-165)
  • Criswell under 3.5 strikeouts (-160)

Sascha Paruk’s 2024 MLB betting record: 12-8 (+1.18 units)



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