Whether they root for the north siders or south siders, nearly every baseball fan in Chicago circles the White Sox- Cubs matchups every year on their calendar. It feels like the matchup has seen it all over the past few years, from big hits to dominant pitcher performances, to bench-clearing brawls, the crosstown rivalry never fails to bring epic moments. As the Cubs and White Sox get set to butt heads on the south side this weekend, the matchup brings an unusual new level of stakes. The White Sox completed the sweep of the Royals Thursday night to reach an over .500 record in May for the first time in a few years, and this type of heater from both Chicago things is rarer than you think.
The White Sox sweep the Royals, pushing their record to 22-21, setting up a great matchup for rivalry weekend against the Cubs. Incredibly, the last time the two teams faced each other when BOTH teams were above .500 was June, 2008. (excluding 2020).
— Jesse Rogers (@JesseRogersESPN) May 15, 2026
It’s hard to believe, but it’s true. This will be just the second time since 2008 that the White Sox and Cubs will play each other with both teams over.500. The first, in the shortened 2020 season, came without fans in the stands to add to the rivalry. Both the Cubs and White Sox made the postseason in 2020 for just the third time in history, with the first coming in 1906, when the White Sox defeated the Cubs in the World Series. 2008, the last time both clubs have played each other in a full season while over .500, was a playoff season for both Chicago teams, but both exited in the Division series. Neither team was able to advance in the 2020 playoffs either.
White Sox and Cubs recent struggles have hurt the crosstown rivalry
Chicago hasn’t exactly been a hub for winning baseball over the years. The White Sox broke an 88-year World Series drought with their 2005 championship, but they haven’t won a playoff series in the 21 years since. The Cubs’ drought famously reached the century mark before they finally won in 2016, and they’ve made a couple runs since then but to no avail. Both teams currently sit in a playoff position, with the Cubs winning the NL Central and the White Sox landing a wild card spot if the season ended today.
For me, this is the most excited I’ve been for the Crosstown series in a few years. Over the past few years, the excitement hasn’t been there just based on the face that one or both of the teams have been relatively uncompetitive. Whether the White Sox are legitimate postseason contenders this year or not is still up in the air, but there’s no question they have the strongest team they’ve fielded in a few years, and the Cubs look primed for a deep postseason run. It should be a great test for the upstart White Sox.
The White Sox players are feeling it too. Anthony Kay, Thursday’s winning pitcher for the White Sox, spoke after the game about returning to face his former team this weekend.
“It’s going to be fun,” Kay said. “Hopefully this stadium is rocking with a lot of White Sox fans. It will be a special weekend for sure.”
The White Sox are young, hungry, and playing good baseball, and they have more reinforcements on the way with the imminent return of Kyle Teel and call-up of Braden Montgomery. They have a chance to make a statement against a very strong Cubs team this weekend and let the league know that they should be taken seriously. Let’s hope the boys are up for the challenge.
Add us as a preferred source on Google