About the Chicago White Sox vs. Chicago Cubs Rivalry

By Amelia Walker Senior Content Writer Updated: 10 January 2024

Amelia Walker Senior Content Writer

Amelia Walker is a Senior Content Writer at Betting.US. She has a law degree and deep knowledge of the gambling laws in the United States. Her mission is to keep players informed about responsible gambling, while her passion for sports helps her create useful guides. Amelia has over a decade of experience in betting, which has positioned her as a trusted voice among our readers.

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Chicago White Sox vs Chicago Cubs – A Relentless MLB Rivalry

• History & Previous Meetings
• Chicago White Sox Memorable Moments
• Chicago White Sox Form and Season
• Chicago Cubs Memorable Moments
• Chicago Cubs Form and Season

Chicago White Sox and Chicago Cubs share one of the most intense interleague rivalries in Major League Baseball (MLB). The White Sox are members of MLB’s American League (AL) Central Division, while the Cubs are members of the National League (NL) Central Division.

The White Sox-Cubs rivalry is often known as the “Crosstown Showdown” or “Crosstown Classic.” The games generate a lot of competition and excitement among baseball fans based in Chicago. The fans of each team refer to the opposing supporters as “enemies,” and their games are marked with trash talks and rivalry banter.

The rivalry adds to the rich baseball tradition in the city, and their matchups continue to be a major highlight of each MLB season.

History & Previous Meetings

The rivalry between the Chicago White Sox and the Chicago Cubs began with their first meeting in 1906. The White Sox won that match 2-1.

Since the beginning of the interleague, there have been eight 3-game sweeps. The Cubs swept the series four times (1998, 2004, 2007, and 2008), and the White Sox matched that with as many series (1999, 2008, 2012, and 2021).  The Cubs have swept the season twice (1998 and 2013).

In the 2023 MLB Season, the White Sox led the regular season series 74-68.

Chicago White Sox Memorable Moments

The Chicago White Sox have produced some memorable moments in their decades-long rivalry over their arch-rivals. It began in the 1960 World Series, where the White Sox defeated the Cubs in the first-ever “Subway Series” to determine the best team in Chicago. The White Sox clinched the series 4-2 and became the World Series Champions.

In the 2008 Crosstown Classic second game, the White Sox pulled off a thrilling 11-7 victory over the Cubs. White Sox slugger Jim Thome hit a walk-off home run in the bottom of the 15th inning, marking one of the longest and most exciting games of the rivalry.

In the 2017 Crosstown Classic, The White Sox defeated the Cubs 3-1 in the first game of a four-game series.  White Sox pitcher Anthony Swarzak played an instrumental role in delivering a solid performance and securing the win.

The White Sox and the Cubs faced off in a three-game series during the pandemic-shortened 2020 season. The White Sox won the first two games, and the third turned out to be memorable, as Eloy Jimenez hit a game-winning home run against his former team.

In the 2021 Crosstown Classic, the White Sox displayed their dominance to clinch a 10-0 victory. White Sox pitcher Lucas Giolito put a stellar performance on display with a complete shutout while their offense exploded to secure the victory. It’s safe to say that whoever wagered on the event got great odds at the best MLB sportsbooks.

Chicago White Sox Form and Season

The Chicago White Sox featured in their 123rd season in the American League and 33rd at Guarantee Rate Field. The club played under the management of Pedro Grifol for the first time.

In August, after starting the season 49-76, general manager Rich Hahn and Executive Vice President Kenny Williams were given the sack. The White Sox failed to improve their 81-81 record from the previous season and were out of playoff contention in September, thus not being a part of the action in Illinois online sports betting sites.

Chicago Cubs Memorable Moments

The Chicago Cubs have also registered their fair share of memorable moments against their nemesis. One such enthralling encounter came in the 2008 Crosstown Classic, where the Cubs defeated the White Sox 11-7 in a thrilling 15-inning contest. This game was memorable due to its multiple lead-changing scenarios and dramatic moments, including a game-tying home run by Aramis Ramirez in the ninth inning and a game-winning home run by Reed Johnson in the 11th.

In the 2009 Crosstown Classic, the Cubs secured a 6-5 victory against the White Sox at U.S Cellular Field. It was an intense matchup as the Cubs were trailing by two runs in the top of the ninth inning. With two outs, Alfonso Soriano hit a game-tying three-run home run to send the game into the extra inning, where the Cubs eventually emerged victory.

In the 2013 Crosstown Classic, the Cubs defeated the White Sox 8-3. It was a memorable game because Starlin Castro and Nate Schierholtz hit a grand slam each in the same game, which is a rare occurrence in the team’s history.

In the 2016 Crosstown Classic, the Cubs defeated the White Sox 3-1, courtesy of a game-winning home run in the eighth inning by Kris Bryant to break a 1-1 tie.

Chicago Cubs Form and Season

The 2023 season was the 152nd for the franchise, the 148th in the National League, and the 108th for the Cubs at Wrigley Field. The Cubs were led by David Ross for the fourth successive season and played as members of MLB’s National League Central Division.

The Cubs finished the season 83-79 in second place and failed to make it to the playoffs for a third consecutive season.