Brewers vs. Cubs Prediction, MLB Picks for Monday, August 31

First pitch for the Milwaukee Brewers vs. Chicago Cubs game is set for 7:40 p.m. ET on Monday, August 31, with the Cubs entering as favorites and returning a 1.85x payout if they win, via PrizePicks.

Today’s matchup is game one of a four-game series between these division rivals. The Brewers currently hold a 4-2 lead in the season set with six games remaining. Can the Cubs chip away at that lead in front of their home crowd?

Below, we'll break down our Brewers vs. Cubs prediction and picks for Monday’s MLB game, including the spread, over/under, and key player picks for PrizePicks.

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Brewers vs. Cubs, Winner Payout, Over/Under – Monday, August 31

The Brewers continue to roll. They not only own the best record in baseball at 85-52, but they also have the best run differential (+177). They're simply one of the most complete teams right now, playing elite defense, making tons of contact on offense, and having one of the best overall pitching staffs in baseball.

They'll be sending LHP Kyle Harrison (3.08 xFIP) to the mound tonight. Harrison has been phenomenal for the Brew Crew, owning a minuscule 2.79 ERA to go along with an elite 11.06 K/9. He's had a bit of an issue with home runs to RHB (1.6 HR/9), so he'll have to solve that in Wrigley tonight with projected 10 mph winds blowing out to CF.

The Cubs have had an impressive season of their own at 77-60 with a +127 run differential. They're eight games behind the Brewers for first place in the NL Central.

Chicago will have RHP Clay Holmes (3.75 xFIP) toe the rubber tonight. Holmes is a bit of a throwback hurler in the sense that he doesn’t have elite velocity or strikeout rates, instead generating the most ground balls in baseball. He's a perfect fit for a Cubs team that leads MLB in defensive runs saved (101).  

Brewers vs. Cubs Winner Payout, Over/Under – Monday, August 31

The Cubs enter Monday’s game as small home favorites against the Brewers, returning a 1.85x payout if they win outright, via PrizePicks Team Picks.

Here are the full payouts for the Brewers vs. Cubs game on PrizePicks.

Play the Brewers vs. Cubs spread or over/under on PrizePicks Team Picks to earn real money — available in 36 states!

Team Picks data is live at the time of writing and is subject to change.

Brewers vs. Cubs Prediction on Winner – 8/31/26

Here are the key game stats and trends behind our Brewers vs. Cubs prediction on the winner for Monday, August 31.

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Unless otherwise noted, data used in this article is from Baseball Savant or FanGraphs.

• These two teams are incredibly evenly matched, but a few things about tonight’s starting pitching matchup make me like this spot for the Cubs to chip away at the Brewers' lead in the division.
• I'm concerned about Kyle Harrison’s home run rates. He has a 2.38 HR/9 rate on the road against RHB, which could be a big problem in Wrigley's hitter-friendly conditions tonight.
• The Cubs are third in baseball with 187 home runs and are built to take advantage of those poor fly ball rates.
• The Brewers, on the flip side, are dead last in home runs, instead opting to be a pesky offensive team that makes a ton of contact and doesn’t strike out.
• This style actually plays into the hands of Holmes, who induces the type of contact (60% ground ball rate) that goes into the hands of his elite defense.

Brewers vs. Cubs Picks, Player Stats for PrizePicks: 8/31/26

Here are the top Brewers vs. Cubs picks to target on Monday, August 31. Today’s MLB picks for PrizePicks include Kyle Harrison and Clay Holmes.

Brewers P Kyle Harrison vs. Cubs: 5 Strikeouts

• Harrison owns a 12.32 K/9 and 2.24 xFIP at home but just a 9.52 K/9 and 4.11 xFIP on the road.
• The Brewers have been fairly careful with Harrison’s innings recently. In his last six starts, he's thrown 90 pitches twice, and in the other four he's averaged just 72.5.
• The Cubs have been doing a fantastic job of making contact and being disciplined, posting a 19.1% strikeout rate over the last two weeks, ninth-best in baseball.
• Chicago is better against LHP with a 126 wRC+ against southpaws (best in baseball) compared to a 111 wRC+ against RHP (third).

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Cubs P Clay Holmes vs. Brewers: 15.5 Pitcher Outs

• Since being acquired from the Mets, Holmes has only seen his pitch count increase in each start, topping out at 93 in his last start, a 7-inning blanking of the Diamondbacks.
• Holmes limits free passes, with his 2.97 BB/9 being the lowest mark in the last four years of his career. That aforementioned ground ball rate can also lead to quite a few double plays.
• Holmes has cleared this projection in three straight starts.
• The Cubs' bullpen hasn’t been awesome recently, ranking just 17th in xFIP over the last two weeks. This could lead skipper Craig Counsell to roll with his starter a bit longer if he's preventing damage.

Add Clay Holmes to your PrizePicks Lineup now.

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What better way to start the week than an exciting rivalry game in the heart of Chicago? Will the Brewers continue their dominant ways this season, or will the Cubs kick off what could be one of the great late-season divisional comebacks with a massive win?

Don’t wait until lock — make your Brewers vs. Cubs picks on PrizePicks now and earn real money if you’re right.

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