Cubs vs Red Sox Prediction, Picks, and Odds for Today's MLB Game

With a pitching matchup that is quite lopsided when you delve into the peripherals, Rohit Ponnaiya has a clear side for this afternoon's showdown at Fenway Park. Read more in our Cubs vs. Red Sox betting picks.

Rohit Ponnaiya - Betting Analyst at Covers.com
Rohit Ponnaiya • Betting Analyst
Apr 27, 2024 • 12:23 ET • 4 min read
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This article contains predictions for an old game!

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Mike Tauchman Chicago Cubs MLB
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The Chicago Cubs and Boston Red Sox face off at historic Fenway Park on Saturday.

MLB odds have the Cubs as slim -115 road favorites with the Over/Under at 8.5 for this interleague clash. Here are my best free Cubs vs. Red Sox predictions and MLB picks for April 27.

Cubs vs Red Sox prediction

My best bet
Cubs moneyline (-115 at bet365)

My analysis

Both of these teams have banged-up rotations, which is why they are both starting young right-handers that have recently been used in the bullpen.

The Boston Red Sox will give the ball to Josh Winckowski, who pitched to a 5.89 ERA across 14 starts in 2022. He threw 84 1/3 innings last year almost entirely as a reliever and lowered his ERA to 2.88 with an xERA of 3.82. The righty owns a 4.20 ERA in 15 innings this year and he's coming off his first start, pitching 3 1/3 innings of one-run ball against the Pirates. 

Meanwhile, the Chicago Cubs are starting 24-year-old rookie Ben Brown, who entered this season as the No. 9 prospect in their system. He was rocked for six runs in 1 2/3 innings against the Rangers in his MLB debut but has settled into a groove ever since, allowing just nine hits and a pair of runs through 17 2/3 innings in his last five outings (three starts). 

When it comes to hitting the ball, the Cubs have the edge. They are fifth in the majors in scoring (5.38 runs per game) and OPS (.330). Meanwhile, the Red Sox are 15th in runs per game (4.33) and 13th in OPS (.308), with those numbers plummeting to 3.27 and .616 at Fenway. This is a Boston lineup that strikes out at the fourth-highest rate in the majors (26.2%) and ranks among the worst 10 teams in batting average (.235) and hard-hit rate (37.4%). 

I'm not sold on Winckowski being able to successfully make it through a lineup more than twice, and I have been impressed with Brown after an ugly debut. With the Cubs lineup also making better contact, I'll back them at close to a pick'em price.

Cubs vs Red Sox same-game parlay (SGP)

Cubs moneyline

Rafael Devers Over 1.5 total bases

Mike Tauchman Over 0.5 hits

Rafael Devers began the season mired in a slump, which may have been due to a nagging shoulder injury. However, since coming off a short stint on the IL with a different issue, Devers has gone 7-for-13 at the dish over the last three games. The two-time Silver Slugger winner has slugged .570 with the platoon advantage since the start of the 2019 season.

Mike Tauchman is another left-handed hitter with the platoon edge in this contest. The Cubs outfielder has picked up a hit in eight of his last nine games and is batting .429 over that span.

Learn how to bet a same-game parlay with these helpful tips and strategies.

Cubs vs Red Sox odds

Cubs vs Red Sox live odds

Cubs vs Red Sox opening odds

  • Run line: Chicago -1.5 (+135) | Boston +1.5 (-165)
  • Moneyline: Chicago -115 | Boston -105
  • Over/Under: Over 8.5 (-120) | Under 8.5 (+100)

Cubs vs Red Sox spread and Over/Under analysis

  • The line opened with the Cubs at -115 and briefly went up to -125 before buyback on the home side brought it back down to the opening number.
  • The Cubs have gone 17-7 with a run differential of +42 in their last 24 games.
  • The Red Sox are just 3-8 at home with a run differential of -28.
  • Boston continues to be the worst fielding team in the majors, committing an MLB-high 0.89 errors per game.

Cubs vs Red Sox trend

The Red Sox have cashed the moneyline in just 57 of their last 127 games (-22.75 Units / -14% ROI). Find more MLB betting trends for Cubs vs. Red Sox

Cubs vs Red Sox game info

Location: Fenway Park, Boston, MA
Date: Saturday, 4-27-2024
First pitch: 4:10 p.m. ET
TV: MARQ, NESN
Cubs starting pitcher: Ben Brown
(0-0, 3.72 ERA)
Red Sox starting pitcher: Josh Winckowski
(1-1, 4.20 ERA)

Cubs vs Red Sox latest injuries

Cubs vs Red Sox weather

Not intended for use in MA.
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Betting Analyst

With a background playing soccer, rugby, and boxing, combined with a journalism degree, it's little surprise that Rohit gravitated towards the world of sports betting. He specializes in betting on UFC and college basketball, two sports where the eyeball test can tell you a lot more about matchups than any analytics. Rohit has years of experience handicapping NFL and NBA games as well as niche betting markets such as politics and Oscar odds. He's also the resident CFL expert and formerly hosted "The Chez and Ro Show" with former CFL star Davis Sanchez.

You can catch Rohit breaking down every UFC event with Joe Osborne on "P4P Picks" on the Covers YouTube channel and he also has regular appearances on "Before You Bet" with Joe. In addition, he's a regular guest on "By The Book" on the Monumental Sports Network and makes guest appearances on VSIN's "The Handle" and CBS Sports.

Rohit primarily makes his bets at bet365, which offers a wide variety of prop markets, but also has accounts at several others so he can shop around for the best prices. For Rohit, bankroll management is key. He believes you should never bet what you can't afford to lose and maximize those few betting opportunities where books misprice a line.

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