Who are Chicago White Sox biggest rivals?

Chicago White Sox biggest rivals are the Chicago Cubs.

If you’ve never heard of the White Sox-Cubs rivalry, you’re not alone. It’s known by a variety of names, including “The Crosstown Showdown,” “The Windy City Showdown,” “The Red Line Series,” and “The City Series,” among others.

Aside from Wrigley Field, where the Chicago Cubs of the National League play their home games, there is also Guaranteed Rate Field in the city of Chicago where the Chicago White Sox of the American League play their games.

“North Siders” and “South Siders” have become synonymous with the teams and their followers, creating a longstanding rivalry. In addition to making stops at Wrigley Field on Addison Street and Guaranteed Rate Field on 35th Street, the Red Line of the Chicago Transit Authority travels north and south through the city’s neighborhoods.

Interestingly, this rivalry extends back to 1906.  It was the first time two teams from the same city faced off in the World Series. White Sox beat the Cubs, who had a record of 116 wins throughout the season, 4 games to 2 in the best-of-seven series.

From 1985 through 1995, the White Sox faced off in the Crosstown Classic, where the White Sox were undefeated at 10–0–2.

There are presently 49–44 in favor of the White Sox in the regular-season series. Since the start of interleague play, the Cubs have swept six series, in 1998, 2004, 2007, 2008, and both series in 2013, while the White Sox have swept three, in 1999, 2008, and 2012 respectively.