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Both Chicago Baseball Teams Are in Playoff Position. That Hasn’t Happened Since 2008.
Records current as of Aug. 26, 2026
The Cubs are 76-57 and effectively locked into the National League playoff field. The White Sox are 69-63 and leading the AL Central.
It is late August, and both Chicago baseball teams are playing games that matter. If you have to think for a moment about the last time that was true, you’re not alone.
Two entirely different roads here
For the Cubs, this was the plan. Chicago has operated at championship-or-bust level since spring training, made the playoffs last October, won a Wild Card Series against San Diego and lost a five-game Division Series to Milwaukee. Jed Hoyer spent the deadline adding Kevin Gausman, Clay Holmes and two more arms to a roster that was already winning at a 91-win pace. Contending in August was the baseline expectation, not the achievement.
For the White Sox, nothing about this was the plan.
This is a franchise that lost 101 games in 2023, then 121 in 2024 — the most in modern major league history — then finished under .500 again in 2025. Three straight seasons of triple-digit or near-triple-digit losses. In 2024 they were eliminated from playoff contention on Aug. 17, earlier than any team since divisional play began.
They have been in first place every day since July 4.
The Crosstown Classic actually meant something
The two teams split the season series, with the final three games at Wrigley completing this year’s edition — in the 20th anniversary season of “The Punch,” for those keeping historical score.
Series like that are usually an exhibition with a rivalry label attached. This one wasn’t. Both clubs came in making a genuine postseason push, which is the version of the Crosstown Classic the city almost never gets. The White Sox left it holding a four-game division lead. The Cubs left it with the fourth-best record in the National League.
What each team still has to do
They’re chasing different things, which is part of what makes this interesting.
The Cubs’ work is about position, not survival. Milwaukee sits at 81-51 and has been the better team all season. Catching the Brewers is a long shot, and falling short likely means the wild card round — the same path that ended last October early. The questions are about Gausman settling in after three uneven starts, Holmes building back from a leg injury, and whether the best defensive infield in baseball stays intact through September.
The White Sox’ work is about holding on. The 5.5-game cushion built by sweeping Detroit is down to 2.5. Cleveland has won five in a row and seven of ten, and the Guardians bring something Chicago’s young roster doesn’t have: recent experience in a tight September race. Davis Martin is on the injured list and the rotation needs him. Every remaining division game is a leverage game.
One team is trying to arrive in October in the right shape. The other is trying to get there at all.
Why this matters beyond the standings
Chicago is a baseball city that has spent most of the last decade watching one team at a time — and often neither. The North Side had its era. The South Side had its collapse. The overlap has been thin.
An October where both teams are playing would be the first genuinely citywide baseball month in a long time. The odds of that happening are decent on one side and precarious on the other, which is roughly the right amount of tension for a last week of August.
Thirty-odd games left. Both scoreboards worth checking.
Chicago Sports Wire covers the Cubs and White Sox all season. See the Cubs schedule and White Sox schedule for first pitch times and broadcast info.