Cubs vs Brewers Odds, Picks, & Predictions

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29 September 2023

Cubs vs Brewers Odds, Picks, & Predictions

The Cubs are in desperation mode while the Brewers have nothing to play for, yet oddsmakers see this tilt as a coin-flip. Our MLB betting picks can't follow that logic, and think there's a strong case for Chicago on Friday night.

The Chicago Cubs will look to stay in the race for the final National League Wild Card spot as they visit the Milwaukee Brewers on Friday night.

The Brewers (90-69) clinched the NL Central earlier this week, and are locked into the No. 3 seed in the NL playoffs. The Cubs (82-77) have lost three in a row, and are now in danger of missing the postseason as they sit a half-game behind the Miami Marlins for the final Wild Card berth.

The MLB odds have tonight’s game listed as a toss-up, but this is a matchup that Chicago absolutely needs to win. We’ll discuss whether they can get a victory in our free MLB picks and predictions for Cubs vs. Brewers on September 29.

Cubs vs Brewers odds

Cubs vs Brewers predictions

The Cubs are coming off a three-game sweep at the hands of the Braves, but that hasn’t yet dealt a death blow to their playoff chances. While Chicago is just 6-13 in its last 19 games, it still sits within striking distance of the final Wild Card spot with just three games left to play. But with Miami holding the tiebreaker over Chicago, the Cubs can’t afford any more losses.

Chicago may get something of a break this weekend. They’ll be playing their final three games against a Brewers team that has nothing to play for, as they’ve already clinched the division but can’t move into a first-round bye. Even better, they won’t have to face off with either Brandon Woodruff or Freddy Peralta, both of whom Milwaukee manager Craig Counsell has confirmed will not pitch before the end of the season.

Instead, the Brewers are handing the ball over to righty Colin Rea for Friday’s game. Rea has done a good job of showing he can compete at the major league level after pitching in Japan last year, but he’s hardly been impressive as a starter. In 21 starts, he’s posted an ERA of 4.97, putting up a 5-5 record in that role. Milwaukee has sent Rea back and forth between Triple-A and MLB multiple times this year, and he doesn’t figure to play a big role in the Brewers’ postseason plans.

Rea is the kind of pitcher that the powerful Cubs offense should be able to score against. Even in the sweep in Atlanta, Chicago was able to average 4.7 runs per game, and we can expect that number to go up against a Milwaukee team that will be limiting or completely resting all of its best arms heading into the playoffs.

The Cubs should also get solid pitching out of veteran Kyle Hendricks, who has put in another solid year for Chicago. The 33-year-old has also thrown well down the stretch, putting up a 3.16 ERA over his last nine starts heading into Friday’s game.

Sportsbooks have pegged this game as a virtual toss-up, with some giving the Cubs the slightest of edges. I’m more bullish on Chicago tonight, as they’ll be playing with all of their weapons in order to keep themselves in the playoff race. I expect the Cubs to grab a win tonight and keep their postseason hopes alive for at least one more day.

My best bet: Cubs moneyline (-108 at FanDuel)

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Cubs vs Brewers same-game parlay

Cubs moneyline

Over 8.5

Cody Bellinger 1+ RBI

For my same-game parlay, I am building around my expectation that the Cubs will be able to score runs off of Rea.

First, I’m going to take the Over at 8.5 runs. With Rea and Hendricks on the mound, both teams should be able to get on the board early, and I don’t expect Chicago to stop scoring there. With the Brewers at least contributing a couple of runs to the total, the Over feels like the right side of the line.

Finally, I’ll take Cody Bellinger to record an RBI. While the Cubs offense has struggled as of late, Bellinger still has RBIs in two of their last four games.

With this being a likely breakout game for the Chicago offense and plus money available on this prop, I’m happy to back Bellinger to knock in a run to round out our SGP.

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Cubs vs Brewers moneyline and Over/Under analysis

The Cubs and Brewers opened this game on mostly even terms, though some books made the Cubs a slight -115 favorite. Those lines are largely unchanged as of Friday morning, which means you can find Milwaukee at -105 at many books.

The Brewers have been a solid moneyline team this year, making more than nine units in profits for their backers. The Cubs have been treading water, and are currently down 1.5 units on the season.

I’ve made the Cubs my best bet for the night, due in large part to the fact that they’re the only team in this game that’s going all-out to win. With many Brewers pitchers resting or taking only limited roles in the final series of the year, a Cubs offense that averages 5.08 runs per game should break out in a big way. Take the Cubs on the moneyline tonight.

The total on tonight’s game opened at eight runs, and that remains the consensus Over/Under at almost all sites. The most popular line has the Under as a slight favorite at -115, though you can find it at -110 by shopping around. Meanwhile, the Over is available at -105 at the majority of books.

The Cubs have scored a lot of runs this year, and the Over has a slight edge in their games, going 78-75 when Chicago plays. Milwaukee has been an Under team this year, with the Under posting a 81-70 record in its games.

Tonight, I’m looking at a game that should have plenty of runs scored. Rea shouldn’t be able to hold down the Chicago offense, and while Hendricks is a solid pitcher, it’s hard to see the Cubs completely shutting down the Brewers at home over nine innings. I’m leaning strongly towards the Over at eight runs, and would even consider playing it at 8.5.

Trend to know

The Cubs are 4-2 in their last six games against the Brewers. Find more MLB betting trends for Cubs vs. Brewers

Cubs vs Brewers game info

Starting pitchers

Kyle Hendricks (6-8, 3.66 ERA): Hendricks has been a mainstay in the Cubs rotation since joining the major league team in 2014. While this hasn’t been his best year ever, it’s a nice bounce back from two seasons in which he posted an ERA of 4.77 or higher. In his last start, Hendricks allowed three runs (one earned) on seven hits over six innings in a loss to the Pittsburgh Pirates.

Colin Rea (6-6, 4.74 ERA): After spending 2022 playing with the Fukuoka SoftBank Hawks of Nippon Professional Baseball in Japan, Rea signed a minor league deal with the Brewers in the offseason. Rea bounced back and forth between the major league squad and Triple-A Nashville, but ultimately has found success in 25 appearances — including 21 starts — with Milwaukee this year. In his last appearance, Rea came out of the bullpen on September 26, throwing a hitless inning against the St. Louis Cardinals.