Crosstown Classic

Lore & Background

The terms 'North Siders' and 'South Siders' are synonymous with the respective teams and their fans, setting up an enduring rivalry. Fans from the North Shore and Chicago's northern suburbs tend to support the Cubs, whereas fans from the south side of Chicago tend to support the White Sox. As of May 17, 2026, the Cubs lead the regular season series 78–77. There have been nine 3-game series sweeps since interleague play began: five by the Cubs in 1998, 2004, 2007, 2008, and 2025, and four by the White Sox in 1999, 2008, 2012 and 2021. There have been three season series sweeps, all by the Cubs in 1998 (3 games), 2013 (4 games) and 2024 (4 games). The Chicago Transit Authority's Red Line train has stops within a block of both ballparks: Addison station for Wrigley Field and Sox–35th station for Rate Field.

Reader's Guide

While teams in New York City (such as the Yankees, Giants, and Brooklyn Dodgers) routinely played against each other in World Series matchups throughout the 1940s and 1950s, the two Chicago teams only met once in the 1906 World Series, a celebrated event that seemingly put the city on hold for a full week. The heavily favored but young Cubs (who had won 116 games in the regular season) lost in six games to the veteran and pitching-strong White Sox, the 'Hitless Wonders'.

From 1903 until 1942, excluding the years one team or the other won the pennant, the Cubs and White Sox played each other in a best-of-seven postseason City Series. These series were officially sanctioned by the National Baseball Commission and, later, the Commissioner of Baseball. The first series was played in 1903 and was a best-of-15. That year, the Cubs had a 6–3 series lead before the White Sox came back to force a 7–7 tie.

Thanks to a rainout, they did not play the decisive 15th game as the players' contracts expired on October 15. Starting in 1905, the series became best-of-seven and remained that way until 1942. In all, they played 25 City Series with the White Sox winning 18 and the Cubs winning six to go along with the tie of 1903. The 1912 version marked the first time in a Major League Baseball postseason series that a team overcame a 3–0 series deficit as the White Sox won the final four games of the series. 1985 saw the start of an annual 'Windy City Classic' charity game.

The series alternated between the respective teams' ballparks, with Comiskey Park hosting the first year followed by Wrigley Field the next. The Sox would go 10–0–2 in this affair that lasted through 1995 (two games were played in 1995). One exhibition between the teams at Wrigley Field on April 7, 1994, was notable for the White Sox having Michael Jordan playing right field – Jordan was playing for a White Sox minor-league affiliate, the Birmingham Barons, during the first of his nearly two seasons of his first retirement from the NBA before his comeback with the Bulls.

Since inter-league play began in 1997, the White Sox and Cubs have routinely played each other four or six times each year (one two or three-game series at each stadium). Based on the availability of tickets and the prices offered through ticket brokers, these games are among the most anticipated of the season.

Did You Know?

• The rivalry turned physical on May 20, 2006, when a brawl broke out during a White Sox-Cubs game at U.S. Cellular Field.
• In 2006, Pierzynski was named one of the five American League players in the All-Star Final Vote.