Updated August 31, 2026
The Milwaukee Brewers and Chicago Cubs will open a big NL Central series Monday night at Wrigley Field, with first pitch set for 6:40 p.m. CDT. Milwaukee comes into the series at 85-52 and sitting comfortably atop the division, eight games ahead of the 77-60 Cubs.
Kyle Harrison (10-3, 2.79 ERA) gets the start for Milwaukee, while Chicago will counter with Clay Holmes (5-6, 2.26 ERA). With just a month left in the regular season, the Cubs have plenty of work to do if they want to make the NL Central race interesting, and this four-game series gives them a chance to cut into Milwaukee’s lead.
Let’s preview Monday’s series opener, make our Brewers vs Cubs prediction, and break down a few of the biggest storylines heading into Game 1.
I’m taking the Cubs to win at home against their division rival on Monday night. Chicago is currently priced at 51¢ on Polymarket, and I like the setup for the Cubs despite their recent struggles.
Yes, Chicago has been in a bit of a funk lately, losing three straight series. That includes dropping two of three to the struggling Reds over the weekend and allowing 22 runs to a Cincinnati offense that ranks in the bottom third of MLB in just about every major offensive statistical category.
Still, I like the Cubs to bounce back here. They may not have a particularly realistic shot at overcoming an eight-game deficit and catching Milwaukee in the NL Central, but this series could be a good dress rehearsal for October. Both teams are in a strong position to make the playoffs, and there’s a very real chance they could meet again in the NLDS.
Chicago also has one of its best arms on the mound in Clay Holmes, who comes into Monday pitching some of his best baseball of the season. Holmes has posted a 1.96 ERA and 0.96 WHIP in August, and I’m expecting another solid outing from him at Wrigley.
That said, if you’re worried about the Cubs’ bats struggling to get going, the Under 9.5 at 51¢ on Polymarket is another option I like. That also lines up with the ATS.io Quantitative Model, which projects a total of just seven runs to be scored. Check out our full Brewers vs Cubs prediction for more analysis and the latest matchup data.
We have to start by talking about Pete Crow-Armstrong, who has been on an absolute tear lately. PCA is 6-for-11 over his last two games with a ridiculous five home runs and eight RBIs, including three homers on Saturday and two more on Sunday.
The 24-year-old has put together an incredible season overall, hitting .283 with a .954 OPS, 32 stolen bases, and an MLB-best 8.5 WAR. He’s now the clear favorite to win NL MVP, with “Yes” currently trading at 89.1¢ on Polymarket, implying roughly an 89% chance of taking home the award. That’s pretty remarkable considering he shares the National League with Shohei Ohtani, who has made a habit of putting up video-game numbers as both a hitter and pitcher.
Crow-Armstrong will look to keep his hot streak going Monday and help a Cubs offense that has been putting up some huge numbers lately. Chicago has averaged 8.57 runs per game over its last seven, including 19- and 17-run performances, showing just how quickly this lineup can explode on any given night.
The challenge, however, is that PCA and this red-hot Cubs offense will be going up against Kyle Harrison, who has been excellent for Milwaukee this season. Harrison is 10-3 with a 2.79 ERA and 1.12 WHIP, and he’s been even better lately, giving up one run or fewer in three of his four starts in August.
He’s also had plenty of success against the Cubs already this year. Harrison has faced Chicago twice, allowing just two earned runs on five hits across 12 innings while racking up 20 strikeouts.
That could be especially important Monday with the weather at Wrigley looking pretty hitter-friendly. According to Wrigley Winds, it’ll be around 86 degrees with the wind blowing out to center at 10 mph and gusts up to 23 mph. If there’s someone you’d want on the mound to slow down this dangerous Cubs lineup with the wind blowing out, Harrison is definitely on the short list.
As I mentioned earlier, the Cubs sit eight games behind the Brewers in the NL Central with just about a month of regular-season baseball left. Polymarket isn’t giving them much of a chance to catch Milwaukee, with the Brewers currently priced at about 96¢ to win the division, implying roughly a 95% chance of finishing on top.
Of course, a series win — or perhaps even a sweep — could make things a little more interesting down the stretch. But the much more realistic path for Chicago is through the Wild Card. The Cubs are tied with the Phillies at 77-60 for the top Wild Card spot, though Chicago currently holds the tiebreaker and essentially has a half-game advantage as a result.
That could end up being pretty important. The top Wild Card team gets to host the second Wild Card team for all three games of the opening-round series, giving Chicago plenty of reason to keep pushing even if Milwaukee ultimately runs away with the division. The Cubs are also 4.5 games ahead of the Diamondbacks, who currently hold the third Wild Card spot, and five games ahead of the Padres.
So, while Chicago is still in a pretty comfortable playoff position, it can’t afford to let this current slide continue for too long. Catching Milwaukee may be a long shot, but there’s still plenty at stake over the final month when it comes to playoff positioning and potentially bringing October baseball to Wrigley.
For more picks and analysis throughout the stretch run, check out our daily MLB picks and predictions for the latest games around the league.
