Cubs vs. Brewers Prediction, Odds, Probable Pitchers, Prop Bets for Monday, Sept. 7

Pete Crow-Armstrong and the Chicago Cubs open a major series on Monday afternoon, as they’ll take on the division-leading Milwaukee Brewers for the second series this month.

Both the Cubs and Brewers are in a great spot to make the playoffs, as Milwaukee could finish with the best record in the National League while the Cubbies currently have the top wild card spot.

A pair of lefties are set to take the mound in this series opener, setting up a rematch from Sept. 1. Matthew Boyd (4.05 ERA) gets the ball against Milwaukee’s Robert Gasser (4.57 ERA) with the Brewers set as slight favorites on the road.

The Cubs are seven games out of the NL Central lead, but they have a lot to play for in the wild card hunt since they’re just a half game ahead of Philadelphia heading into Monday’s action.

Here’s a look at the odds, a prop to bet and my prediction for this divisional battle on Labor Day.

Cubs vs. Brewers Odds, Run Line and Total

Odds via DraftKings Sportsbook

Run Line

Cubs +1.5 (-199)
Brewers -1.5 (+163)

Moneyline

Cubs: +105
Brewers: -126

Total

8.5 (Over -106/Under -114)

Cubs vs. Brewers Probable Pitchers

Chicago: Matthew Boyd (8-3, 4.05 ERA)
Milwaukee: Robert Gasser (4-5, 4.57 ERA)

Cubs vs. Brewers How to Watch

Date: Monday, Sept. 7
Time: 2:10 p.m. ESt
Venue: American Family Field
How to Watch (TV): ESPN Unlimited, Marquee Sports Network, Brewers.TV
Cubs record: 81-63
Brewers record: 88-56

Cubs vs. Brewers Best MLB Prop Bets

Cubs Best MLB Prop Bet

Pete Crow-Armstrong to Hit a Home Run (+389)

Can PCA stay hot as he looks to lock up the NL MVP? He’s one of three players I targeted in today’s edition of Daily Dinger – our best home run picks at SI Betting:

Pete Crow-Armstrong is running away with the MVP in the National League, and he’s up to 40 home runs and 96 runs batted in heading into Monday’s marquee matchup with the Milwaukee Brewers.

The Brew Crew have lefty Robert Gasser on the mound in this matchup, and he’s allowed 13 home runs in 17 appearances in 2026. While a lefty-lefty matchup may not seem favorable for PCA, he’s actually hit left-handed pitching better than righties this season.

In 178 at-bats against southpaws, PCA is hitting .298 with 11 home runs and a .947 OPS. Overall, he has a .280 batting average with a .946 OPS in 2026.

Recently, the Cubs star has been on a wild power surge, homering seven times in the last two weeks and 14 times over his last 25 games. He’s an easy bet at nearly 4/1 to keep this hot streak going.

Cubs vs. Brewers Prediction and Pick

The Cubs have hit the OVER in 56.3 percent of their games (the third-highest mark in MLB), and I believe we could have another high-scoring affair on our hands on Monday.

While Chicago has hit the UNDER in 45.7 percent of its games, both of the starters in this matchup have some shaky overall numbers, sitting the 44th percentile in expected ERA or worse. In fact, Boyd ranks in just the 20th percentile in expected ERA and the 16th percentile in expected batting average against.

These are easily two of the best offenses in MLB, as the Cubs are first in Weighted Runs Created Plus (wRC+), runs scored and OPS while also ranking fifth in batting average. Milwaukee isn’t far behind, sitting in third in wRC+, runs scored and batting average while ranking fifth in OPS.

Back on Sept. 1, both of these starters allowed three runs in a game that finished with a 9-4 Brewers win. I think we could see a very similar result on Monday, and we’re getting a better price on the OVEr (-106) than the UNDER (-114) in this series opener.

Pick: OVER 8.5 (-106 at DraftKings)

Odds refresh periodically and are subject to change.

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