White Sox vs. Red Sox Prediction, Odds, Probable Pitchers, Prop Bets for Monday, April 21

Betting odds, pick and prediction for the Boston Red Sox-Chicago White Sox in MLB on Monday morning.

Boston Red Sox starting pitcher Walker Buehler is a solid prop target on Monday morning. / Jonathan Dyer-Imagn Images

The Boston Red Sox wrap up a four-game series with the Chicago White Sox on Monday – Patriots Day in Boston – with an 11:10 a.m. EST start time.

So, MLB bettors can get some picks in early for this one! 

Boston has righty Walker Buehler on the mound as it aims to win for the 13th time this season after dropping Sunday’s matchup. The Sox are currently in third place in the AL East.

Meanwhile, the White Sox have been one of the worst teams in baseball all season long, going 1-8 straight up on the road and 5-16 overall. They are in last place in the AL Central entering this matchup.

Can Chicago build on Sunday’s win, or will Boston close out the series by winning three of four?

Here’s a breakdown of the odds, probable pitchers, best prop bets and my prediction for this morning matchup in MLB. 

White Sox vs. Red Sox Odds, Run Line and Total

Odds via DraftKings Sportsbook.

Run Line 

• White Sox +1.5 (+114)
• Red Sox -1.5 (-135)

Moneyline

• White Sox: +245
• Red Sox: -305

Total

• 9 (Over +100/Under -120)

White Sox vs. Red Sox Probable Pitchers

• Chicago: Jonathan Cannon (0-2, 4.42 ERA)
• Boston: Walker Buehler (2-1,5.53 ERA)

White Sox vs. Red Sox How to Watch

• Date: Monday, April 21
• Time: 11:10 a.m. EST
• Venue: Fenway Park
• How to Watch (TV): MLB Network
• White Sox record: 5-16
• Red Sox record: 12-11

White Sox vs. Red Sox Best MLB Prop Bets

Red Sox Best MLB Prop Bet

• Walker Buehler UNDER 4.5 Hits Allowed (-115)

After a couple of rough outings to open the 2025 season, Buehler has settled in nicely over his last two starts, giving up just seven hits and three earned runs across 11.1 innings of work.

The Red Sox starter has gone UNDER this line in each of those games, and he could be in line for another strong showing against one of the worst offenses in MLB.

Not only do the White Sox have the worst record in the AL, but they are dead last in baseball in hits, batting average and OPS while ranking 27th in runs scored in 2025. 

Buehler should have no problem shutting down this weak offense on Monday morning. 

White Sox vs. Red Sox Prediction and Pick

Even though the White Sox are 0-4 in Jonathan Cannon’s starts this season, he actually hasn’t pitched terribly.

Cannon has two starts where he hasn’t given up a run, and he has allowed three or fewer runs in three of his four outings. That, coupled with Buehler’s recent resurgence, could be a recipe for an UNDER bet on Monday morning.

The White Sox are the worst offense in MLB this season, so it’s hard to see them really pushing this game over this total, and the Red Sox are one of the better UNDER teams in the league in 2025 (12-9-2). 

Both of these teams have bullpens with ERAs that are over 4.00, but I am buying these starters to keep the scoring at a minimum early on. 

Pick: UNDER 9 (-120 at DraftKings)

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Odds refresh periodically and are subject to change.

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