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Milwaukee Brewers vs. Chicago Cubs prediction, pick for Monday 7/28/25

Milwaukee Brewers vs. Chicago Cubs prediction, pick for Monday 7/28/25

Published:

By: Dan Johnson

You know, as a Cubs fan, this whole Brewers standings situation could not be more annoying. Christian Yelich & co. were responsible for the 2017-2020 divisional undoing—with a lot of help from the Cardinals—of the Bryzzo/World-Series-winning era. They never let the Cubs breathe in the NL Central, and so it is this year, somehow, infuriatingly, and most impressively. And now we’ve got the young stud Misiorowski vs. the resurgent Matthew Boyd. We’ll get to the details. Below, I’ve got my preview, prediction, and best bet for this Monday baseball game between the Brewers and the Cubs.

Here’s how I’ll play it. I’ll be pumping out these predictions for individual games all season, with plenty of coverage here on DraftKings Network. Follow my handle @dansby_edits for more betting plays.

Brewers vs. Cubs prediction, preview

At American Family Field, two 62–43 squads meet in a head‑to‑head battle for NL Central supremacy that feels custom‑made for a pitching duel. Matthew Boyd, riding a 23‑inning scoreless streak, toes the rubber for Chicago with a sparkling 2.20 ERA, his left‑handed cutter and changeup mix leaving opponents baffled. Opposing him is Milwaukee’s flamethrowing rookie Jacob Misiorowski, whose upper‑90s heater and slider have generated 40 strikeouts in under 30 innings. Boyd’s veteran savvy clashes with Misiorowski’s raw stuff, but both pitchers have question marks: Boyd’s career 9.95 ERA in Milwaukee dates back, while Misiorowski has been swaddled in pitch‑count limits.

Offensively, Chicago boasts a top‑three slugging lineup anchored by Pete Crow‑Armstrong and Seiya Suzuki, though they’ve struggled against power arms on the road. Kyle Tucker, Ian Happ, and Matt Shaw still round out a deep lineup that might be able to work Mizzy until the Cubs get to the bullpen, but this is a huge spot for a young flamethrower who’s got everything to prove and the runway of opportunities to do it.

The Brewers counter with Jackson Chourio’s 20‑game hit streak and clutch doubles, yet Milwaukee’s bats tend to fall silent versus lefties—something Boyd will exploit. A breeze blowing in and two elite arms on the hill signal a low‑scoring affair. But does it?

Cubs vs. Brewers pick, best bet

Both bullpens rank among baseball’s best, ready to snuff out any fireworks. Everyone expects a classic pitchers’ duel settled by a single run. But these are fantastic offenses, and the line’s gone below 8.0, which, even despite Boyd’s and Misorowski’s fantastic seasons and repertoires, is purely too low.

Take the over on these two offenses, who’ll likely need nine or ten runs total to decide the game.

Best bet: Brewers vs. Cubs o7.5 total runs (-120)

Tail it with me in the DKN Betting Group here!

Dan Johnson has been an editor, writer, and analyst for DraftKings and DraftKings Network since 2024. He’s previously held editorial posts at The Paris Review, Macmillan Publishers, Bedford/St. Martin’s Press, ASSIGNMENT Magazine, and FantasySixPack. You can find his various editorial work & writing (sports-related and non-) at all of the above.
Disclaimer

I am a promoter at DraftKings and am also an avid fan and user (my username is thegreatdansby9) and may sometimes play on my personal account in the games that I offer advice on. Although I have expressed my personal view on the games and strategies above, they do not necessarily reflect the view(s) of DraftKings and do not constitute a representation that any particular strategy will guarantee success. All customers should use their own skills and judgment in building lineups. I may also deploy different players and strategies than what I recommend above. I am not an employee of DraftKings and do not have access to any non-public information.