Cubs vs White Sox: A Historic Chicago Baseball Rivalry

The Windy City Showdown between the Chicago Cubs and the Chicago White Sox stands as one of Major League Baseball’s most renowned and fervent rivalries. Referred to as the Crosstown Classic, this time-honored contest transcends the baseball field—it’s a clash between the North Side and South Side of Chicago, steeped in tradition, pride, and intense competition.

🏟️ Origins of the Rivalry

The competition started to escalate in the early 20th century. Although both teams are based in Chicago, they embody distinctly different neighborhoods and fan cultures. The Cubs, founded in the late 1800s, play at Wrigley Field located on the North Side. Conversely, the White Sox, established in 1900, compete at Guaranteed Rate Field situated on the South Side.

Their only World Series meeting took place in 1906, when the underdog White Sox—known as the “Hitless Wonders”—defeated the formidable Cubs 4–2 to secure the championship. This extraordinary upset sparked decades of baseball drama throughout the city.

⚾ Head-to-Head Record

As of the 2025 season, the rivalry is almost evenly matched:

Cubs lead the all-time regular-season series: 75 victories to 74

Incorporating all matchups: the Cubs are ahead with a record of 77–78

Longest Win Streak: The Cubs currently enjoy an 8-game winning streak in this rivalry

This equilibrium heightens the stakes of every game, as neither team maintains dominance for an extended period.

🌟 Iconic Moments

Throughout the years, Cubs vs. White Sox games have showcased unforgettable moments:

In 1998, Brant Brown achieved a walk-off home run.

2006: Intense brawls and bench-clearing incidents illustrate the seriousness with which players approach this series

During the 2023–2024 season, the Cubs accomplished several series sweeps, showcasing their superiority.

In May 2025, the Cubs achieved a resounding victory over the White Sox with a score of 13–3, featuring an outstanding performance by Pete Crow-Armstrong, who recorded 6 RBIs, alongside Cade Horton’s remarkable debut.

These matchups are filled with passion, from thrilling walk-offs to fervent fan reactions.

🎉 The Significance of This Rivalry

💬 Claiming Bragging Rights

Securing victory in the Crosstown Classic grants fans the privilege of bragging rights throughout the city until the next encounter. For numerous residents of Chicago, this rivalry is deeply personal.

🧑‍🤝‍🧑 Households Divided

A considerable number of families support both teams, resulting in friendly yet occasionally intense rivalries within their homes and workplaces.

🚇 Convenient Access

Both stadiums can be reached via the Chicago Red Line, facilitating easy access for fans eager to fill the stands during these competitive matchups.

🧠 Fascinating Information

The Sole World Series Matchup: 1906, won by the White Sox
Latest Sweep: Cubs, May 2025
Stadium Nicknames:
Wrigley Field: “The Friendly Confines”
Guaranteed Rate Field: formerly referred to as “Comiskey Park”

📺 Watching Alternatives

You can view the Cubs against White Sox games live on:
Marquee Sports Network (Cubs)
Chicago Sports Network (White Sox)
Local Broadcast: WCIU Channel 26