Rivalries

Lore & Background

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 City Series saw the White Sox overcome a 3–0 series deficit to win the final four games—though it's worth noting this was an exhibition series, not an official MLB postseason 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

In Their Own Story

The wind howled off Lake Michigan, carrying the scent of hot dogs and damp concrete into the lower bowl of Wrigley Field. On the mound stood a Cardinals pitcher, his red cap a stark contrast against the ivy-covered brick wall behind him. In the stands, a sea of blue and red clashed, the air thick with the roar of 'Go Cubs Go' battling the rhythmic chanting from the visiting section. A young fan gripped his grandfather's hand, eyes wide as the batter stepped into the box. This wasn't just a game; it was a continuation of a century-old argument that had been passed down through generations. The pitcher wound up, the crack of the bat echoed like a gunshot, and for a moment, time suspended itself between the two cities, united only by the flight of the ball.

Reader's Guide

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.

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 the bottom of the second inning, Brian Anderson of the White Sox hit a sacrifice fly, attempting
• In 2006, Pierzynski was named one of the five American League players in the All-Star Final Vote. Soon afterwards the Chicago White Sox organization began an election campaign using the slogan 'Punch A.J.', inspired by t
• The White Sox have always been located on the south side. At the time the White Sox came to town, the Cubs' home field was West Side Park, in an older section of the city which is now the West Campus of the University of