Red Sox vs. Brewers Prediction, Odds, Probable Pitchers and Prop Bets for Monday, May 26

Betting odds, pick and prediction for the Boston Red Sox-Milwaukee Brewers matchup on Memorial Day.

Boston Red Sox starting pitcher Garrett Crochet is a great prop target on Monday. / Peter Aiken-Imagn Images

Boston Red Sox ace Garrett Crochet will aim to stop a two-game skid on Monday afternoon when the Sox hit the road to play the Milwaukee Brewers.

Milwaukee is currently in third in the NL Central while the Sox slipped to third in the AL East with a loss on Sunday. Boston is under .500, but the AL East has been so weak – outside of the New York Yankees – that the Sox are just a half game out of second in the division. 

Crochet has been lights out for Boston this season, but the Red Sox are still just 6-5 in his 11 outings. Can they improve on that record as road favorites?

Let’s take a look at the latest odds, players to watch in the prop market and my prediction for this interleague clash. 

Red Sox vs. Brewers Odds, Run Line and Total

Odds via DraftKings Sportsbook.

Run Line

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

Moneyline

• Red Sox: -155
• Brewers: +130

Total

• 7.5 (Over -105/Under -115)

Red Sox vs. Brewers Probable Pitchers

• Boston: Garrett Crochet (4-3, 1.98 ERA)
• Milwaukee: Chad Patrick (2-4, 3.23 ERA)

Red Sox vs. Brewers How to Watch

• Date: Monday, May 26
• Time: 2:10 p.m. EST
• Venue: American Family Field
• How to Watch (TV): FDSNW, NESN
• Red Sox record: 27-28
• Brewers record: 26-28

Red Sox vs. Brewers Best MLB Prop Bets

Red Sox Best MLB Prop Bet

• Garrett Crochet UNDER 1.5 Earned Runs Allowed (-120)

This season, Crochet has allowed one or fewer runs in seven of his 11 starts, and he’s posted a 1.98 ERA overall.

Milwaukee’s offense has been pretty subpar in 2025, ranking 25th in OPS and 23rd in batting average. Milwaukee is hitting just .225 as a team against lefties this season. 

I’ll trust Crochet to stay hot, as he’s given up just five runs across four starts in May. 

Red Sox vs. Brewers Prediction and Pick

Earlier today, I shared in SI Betting’s MLB Best Bets column – Walk-Off Wagers – why the Red Sox are worth a bet early with Garrett Crochet on the mound: 

Crochet enters Monday’s start with 1.98 ERA through 11 starts this season, and his underlying metrics back that up. Crochet ranks in the 99th percentile in pitching run value, 73rd percentile in expected ERA and 84th percentile in strikeout percentage.

Now, Crochet gets a shot at a Milwaukee team that is just 25th in MLB in OPS in the 2025 season. 

The Brewers will counter with Chad Patrick on the mound as an extended opener. Patrick has made 10 starts this season after beginning as a bullpen arm, but he’s only pitched through five innings on five occasions. 

He does have a solid 3.23 ERA this season, but the Brewers are just 4-7 in his outings.

Now, Boston is just 6-5 when Crochet is on the mound, but I’m going to leave both bullpens out of this game and simply take the Sox in the first five innings.

Crochet has given up two or fewer earned runs in 10 of his 11 starts, and the Sox have come alive at the plate as of late, ranking seventh in runs scored and sixth in OPS over the last 15 days.

As long as Boston gets its ace a little run support, Crochet should take care of the rest on Monday. 

Pick: Red Sox First 5 Innings Moneyline (-160 at DraftKings)

---

Odds refresh periodically and are subject to change.

If you or someone you know has a gambling problem and wants help, call 1-800-GAMBLER.

Are you new to DraftKings? Sign up today and place a $5 bet to earn a guaranteed $200 in bonus bets. Win or lose, DraftKings will issue six $25 bonus bets instantly.