Brewers vs Cubs Prediction and MLB Tips - 29 June 2026
Last updated: Jun 28, 2026, 6:10PM | Published: Jun 28, 2026, 4:35AM
The Milwaukee Brewers will take on the Chicago Cubs in MLB action at American Family Field on Monday, starting at 4:10am AEST.
Brandon Woodruff (2-1, 3.00 ERA) will start on the mound for the Brewers, pitting him against Ryan Rolison (5-1, 1.82 ERA) for the Cubs.
This article features Stats Insider's top betting tips for the Brewers vs Cubs game, plus the latest betting odds in Australia.
Who Will Win?
Utilising trusted computer power and data, Stats Insider has simulated the result of Monday's Milwaukee vs Cubs MLB game 10,000 times.
Our proven predictive analytics model currently gives the Brewers a 59% chance of defeating the Cubs at American Family Field.
Brewers vs Cubs: Odds
The latest betting odds in Australia for Monday's MLB game at American Family Field are listed here:
- Head to Head: Brewers $1.59, Cubs $2.39
- Line: Brewers -1.5 ($2.24), Cubs +1.5 ($1.67)
- Total (Over/Under 8.5 Runs): Over $1.91, Under $1.91
Odds are correct at the time of publication and subject to change.
Looking at the latest head-to-head odds, the bookmakers currently have the Brewers at $1.59 and the Cubs at $2.39.
The Brewers are 1.5-run favourites against the Cubs, with odds of $2.24 available at TAB.
For the underdog Cubs (+1.5) to cover the line, TAB offers odds of $1.67.
The over/under for total runs scored is set at 8.5 with TAB, which has odds of $1.91 for the over and $1.91 for the under.
According to Stats Insider's analytics model, the Cubs (+1.5) are predicted to cover the line 58% of the time, while the 8.5-run over/under is expected to go over 53% of the time.
Brewers vs Cubs: Best Bets
- Head to Head: Cubs at $2.39 with TAB
- Line: Cubs +1.5 at $1.67 with TAB
- Total Runs: Over 8.5 at $1.91 with TAB
Our Brewers vs Cubs betting tips are based on world-class simulations and betting intelligence to bring you the best possible advice every day of the year.
While the Brewers have a higher chance of winning the game, betting on the Cubs to win is our preferred option because of the 1.1% edge identified when comparing our data-driven probabilities to the odds currently on offer.
Taking advantage of the edges published here at Stats Insider is pivotal to being a profitable bettor in the long run.
Brewers vs Cubs: Prediction
Stats Insider provides full coverage of the Milwaukee vs Cubs game on Monday, including data-driven predictions and live win probabilitiestips.
Remember, our model updates regularly, so refresh this page for the latest betting predictions before the Milwaukee vs Cubs game.
As always, see our Best Bets for betting tips for every MLB game, plus predictions for a wide range of other sports.
Brewers vs Cubs: Essential Details
The game between the Brewers and Cubs at American Family Field is scheduled to commence at 4:10am AEST on Monday.
- Teams: Milwaukee Brewers vs Chicago Cubs
- Date: Monday 29 June 2026
- Time: 4:10am AEST
- Venue: American Family Field
All dates and times mentioned in this article are in Australian Eastern Standard Time (AEST), unless otherwise stated.
Conclusion
Our Milwaukee vs Cubs predictions have been made based on 10,000 data-driven simulations of the game, carefully curated by our team of skilled data scientists and analysts. We use cutting-edge technology and machine learning to ensure our MLB tips are accurate and reliable, giving you the confidence to make informed decisions.
If you choose to use our predictions for betting purposes, it's crucial to gamble responsibly and keep track of your money. For free and confidential support, call 1800 858 858 or visit gamblinghelponline.org.au.
More on MLB
Stats Insider is your home for betting on the MLB in Australia, with the latest MLB betting news, tips for every MLB game, and futures probabilities for the MLB.
