The Cubs have spent September trying to keep their playoff hopes from slipping through their fingers, and the next stretch of the schedule doesn’t offer much relief. Milwaukee is still looming as the biggest obstacle, but it’s not the only club that could complicate Chicago’s path back to the postseason.
The most obvious threat sits right in front of them: the Brewers. Chicago and Milwaukee still have five head-to-head games over the next week, and those matchups may end up deciding the NL Central.
The Brewers have been the class of the division for years, and that’s still the way things look in 2026. If Milwaukee takes care of business against the Cubs, Chicago would need nothing short of a miracle to catch its rival in the standings.
That challenge gets even steeper when you look at the arms Milwaukee can throw out there. The Cubs will lean on an offense that has been powered lately by MVP frontrunner Pete Crow-Armstrong and a resurgent Alex Bregman, but they’ll have to solve Jacob Misiorowski and a Brewers pitching staff that has been hard to shake.
Even if the Cubs can’t climb all the way back into the division race, another October meeting between these teams still feels possible. If that happens, Chicago will be hoping the ending looks a lot different than the one from last fall.
There’s also Cincinnati, where Sal Stewart has turned his rookie season into a full-blown problem for opposing teams. The Cubs’ recent losses to the Seattle Mariners and Reds hurt, especially because those were the kinds of series Chicago needed to squeeze value out of. Instead, they let chances to chip away at Milwaukee slip away.
Now the Reds get their shot at the Cubs mid-month at Great American Ballpark, and Stewart could be right in the middle of it. The NL Rookie of the Year favorite has already cleared the 30-homer mark and driven in more than 100 runs, and if he helps Cincinnati pull off an improbable September sweep, his reputation in the Queen City only gets bigger.
Atlanta is another team Chicago has to keep an eye on, even if the reasons are different. The Braves are in a tight battle for NL East supremacy with a Phillies club that has surged since firing Rob Thompson and bringing in Don Mattingly. That race could go right down to the wire, and it leaves both Atlanta and Chicago with plenty on the line when they meet at Wrigley Field to close out the regular season.
And then there’s the possibility that Willson Contreras could show up at the worst possible time for the Cubs. Picture the final weekend of the season: Chicago is in Boston, fighting to hang onto a playoff spot, and Contreras is back from the injured list and ready to make life miserable for his former team. He’s having a monster season in Boston, with a career-high 4.3 bWAR, and the team expects to get him back before the regular season ends.
For the Cubs, that would be about as uncomfortable as it gets. Contreras has the kind of energy that can tilt a game, and if his return lines up with Chicago’s playoff push, he could be staring directly at the team’s postseason fate.
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The Cubs have already made clear they want Miller to show he can handle back-to-back days before they consider him truly ready, which makes every missed appearance worth watching. An update is expected after the roster expansion period begins, and until then his progress remains one of the quieter but more important bullpen storylines for a club trying to get its relief mix in order. [Read more 🡒]
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Cubs Give New Call-Up A Real Chance To Help Right Away
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Murray is expected to fill the designated hitter spot against left-hander Robert Gasser, a clear sign the Cubs want to see what he can do right away in a meaningful role. Chicago also added right-handed reliever Tyler Ferguson to the active roster, another move that bolsters the bullpen while the club continues to sort out its roster on the fly. [Read more 🡒]