A Cubs Fan's Guide to September: Ranking the 5 Most Important Games Remaining on Chicago's Schedule

Image courtesy of © Mark Hoffman/Milwaukee Journal Sentinel / USA TODAY NETWORK via Imagn Images

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Hard as it is to believe, the 2026 MLB campaign is coming to an end. The Chicago Cubs currently sit with a record of 81-64, meaning they only have 17 games remaining on their regular-season schedule. But despite the fact that October is right around the corner, there are still some very notable games left that all Cubs fans need to tune into.

Some will impact the standings, while others will give Chicago a chance to measure itself against potential playoff opponents. Either way, these contests will determine the North Siders' aptitude ahead of the postseason.

Ranking Cubs' Most Important Games Down the Stretch

#5: September 22nd vs. Miami Marlins

The Marlins are quietly hanging around in the mix for the final National League Wild Card spot, and since we’re still a couple of weeks away from this matchup, that makes it far too early to know exactly where Miami will sit in the standings. But regardless, this is going to be a good test for the Cubs before the postseason begins.

The Marlins have some legitimate talent on their roster, particularly in their starting rotation. Guys like Sandy Alcántara and Eury Pérez are capable of completely taking over a game, and while it’s too early to know who will be pitching for either side, the Cubs could very easily find themselves facing one of Miami’s top arms.

This game is also the first of a series, and getting it started with a win would go a long way. Especially this late in the season, every series against a playoff-caliber opponent feels important. And with the postseason right around the corner, this one has a chance to feel like October baseball.

#4: September 25th at Boston Red Sox

Boston is all but guaranteed a Wild Card spot in the American League and will be the last team the Cubs play during the regular season. The Red Sox have also been arguably one of the hottest teams in baseball throughout the second half, making this a very interesting series for Chicago.

It’s the same thing I just said about the Marlins game—this one is going to feel like postseason baseball, only with the atmosphere of an electric Boston crowd. The Cubs will be playing at Fenway Park in what should be a hostile environment, and winning games on the road against quality teams is something they’re going to have to be able to do if they want to make a deep playoff run.

Obviously, the Cubs won’t face the Red Sox again unless they reach the World Series. But that almost makes this series even more interesting. The regular season will be coming to an end; both teams will already be thinking about October, and the Cubs will have one final opportunity to test themselves against another legitimate playoff team before the games REALLY start to matter.

#3: Wednesday (Sept. 9) at Milwaukee Brewers

Not only are these two playoff teams. Not only are they division rivals. This is going to be a postseason pitching matchup.

Kevin Gausman will take the mound for Chicago against Logan Henderson for Milwaukee, creating a really fun duel between two very different types of pitchers. Henderson has been a breakout for the Brewers as a rookie, establishing himself as another important piece of Milwaukee’s pitching staff. Meanwhile, the Cubs traded for Gausman specifically for games like this.

Chicago didn’t bring him in just to help them beat struggling teams in August and September. They acquired him because they believed he could take the ball in big games and pitch like a frontline starter. And while this isn’t technically a playoff game, it might as well feel like one.

The Cubs, I’m sure, would also love to have this game after Monday’s loss. There’s still plenty of baseball left to play, but bouncing back against a division rival and a quality starting pitcher would be a good sign for a team looking to build momentum heading into October.

#2: Tuesday (Sept. 😎 at Milwaukee Brewers

It’s game two of three between the Cubs and Brewers in Milwaukee, and this matchup is going to be a massive test for Chicago. David Peterson will take the mound for the Cubs, facing off against the virtual lock for the National League Cy Young Award in Jacob Misiorowski. And not to mention—it’s against their division rival currently sitting atop the NL Central.

The Cubs currently sit eight games behind Milwaukee and likely won’t overtake them before the end of the season. So, this game isn’t necessarily about catching the Brewers in the standings. Rather, games like this show you what a team is made of; if the Cubs want to make a deep run in October, they’re probably going to have to go through Misiorowski and the Brewers at some point. And if they do, there’s a very real chance they’ll see a matchup similar to this one.

Misiorowski’s combination of dominance and a 103 MPH fastball presents a challenge unlike almost anyone else in baseball. Facing him now gives the Cubs another opportunity to see exactly what that looks like before the postseason. And more importantly, beating him would give this team a massive confidence boost.

#1: September 16th vs. Atlanta Braves

This game stands out for a couple of reasons.

For one, the Braves are a playoff team. They currently have the lead in the NL East, but even if they don’t win the division, they’ll almost certainly find themselves in the Wild Card picture. And if they’re a Wild Card team, there’s a legitimate chance they could be facing the Cubs in the No. 4 versus No. 5 matchup. That alone makes this game important.

But there’s another reason this matchup stands out. Despite the fact that neither starting pitcher has officially been announced yet, the rotation lines up for Chris Sale to start for Atlanta. And if it wasn’t for Misiorowski and his 103 MPH fastball, Sale would probably be the National League Cy Young frontrunner. Seeing high-level pitching before the playoffs is incredibly valuable, especially if the Cubs wind up seeing Sale again. He’s exactly the type of pitcher Chicago will have to beat if it wants to make a deep run, and getting an opportunity to face him at Wrigley Field before October would be a valuable experience. Just like the rest of the games I’ve mentioned, this one is going to feel like postseason baseball came early.