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What to Know About Cubs–Sox Rivalry

Posted on June 4, 2024   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

Elvis Andrus of the Sox steals second base in the ninth inning as Dansby Swanson of the Cubs takes the throw at Wrigley Field in 2023.

Elvis Andrus of the Sox steals second base in the ninth inning as Dansby Swanson of the Cubs takes the throw at Wrigley Field in 2023. (Jamie Sabau / Getty)

Before the season’s first Crosstown Classic series at Wrigley Field today and Wednesday, we’re brushing up on the rivalry between the Cubs and Sox.

More Than a Hundred Years Ago …

South Side native Charles Comiskey moved his team from Minnesota to Chicago where he became a founding member of the American League. But the city already had the Cubs, the National League team that was far from excited for Chicago to become a two-team town.

Enter the 1906 World Series

The two teams have only met each other once for the baseball championship. Chicagoans were divided — taking sides and making bets. The Sox, the underdogs of the series, ended up clinching the win in Game 6.

More Games, More Beef

  • The post-season City Series ran from 1903 to 1942.
  • The Boys Benefit games were from 1949 to 1972.
  • The short-lived Mayor’s Series in 1981 was the brainchild of former Mayor Jane Byrne.
  • The Windy City Classic was from 1985 to 1994.
  • The Crosstown Classic as we know it today — a couple of interleague games in the season — began in 1997.
Cubs catcher Michael Barrett punches Sox catcher A.J. Pierzynski in 2006

Cubs catcher Michael Barrett punches Sox catcher A.J. Pierzynski in 2006. (Jonathan Daniel / Getty)

Fast Forward to the 2006 On-Field Brawl

You can’t talk about the Cubs–Sox rivalry without talking about the 2006 Crosstown Classic game. Cubs catcher Michael Barrett and Sox catcher A.J. Pierzynski threw punches after the two collided at home plate. The Sox, hot off their 2005 World Series championship, beat the Cubs 7–0.

City Cast

How Sox and Cubs Rivalry Both Divides and Unites Chicago

00:00:00

What to Expect Now?

The rivalry is not as intense as it was once among players or fans. And neither team is on a winning streak. The White Sox have lost the last 11 games and the Cubs haven’t won a series in almost a month.

If only we could take players from both teams to give Chicago a shot at the World Series … CHGO Sports’ Patrick Norton even dreamt up a roster.

Can’t catch the games this week? Watch the North Siders take on the South Siders at the next Crosstown Classic at Sox park Aug. 9–10.

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