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In between the groups meeting in the 1906 World Series and the beginning of inter-league play in 1997, the Cubs and White Sox would regularly meet, typically annual, although only in exhibit matches, which do not count toward the groups' rankings in their respective league standings. [] 1985 saw the start of a yearly "Windy City Classic" charity video game.

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The Sox would go 10-0-2 in this affair that lasted through 1995. (Two games were played in 1995.) One exhibit in between the groups at Wrigley Field on April 7, 1994 was notable for the White Sox having Michael Jordan playing ideal field Jordan was betting a White Sox minor-league affiliate, the Birmingham Barons, during the first of his nearly 2 seasons of his first retirement from the NBA prior to his return with the Bulls.

Based upon the schedule of tickets and the costs provided through ticket brokers, these games are among the most anticipated of the season. In 2008, the teams played each other as leaders of their respective divisions for the very first time ever: the White Sox in the American League Central and the Cubs in the National League Central.

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The Chicago Cubs swept the White Sox in the very first weekend series at Wrigley Field, and the White Sox subsequently swept the Cubs at U.S. Cellular Field throughout the 2nd weekend series, therefore splitting the series 33 and leading to an all-time inter-league series tie of 3333 through 2008. The Crosstown Cup trophy was introduced in 2010 and the White Sox won the prize the first three seasons before the Cubs lastly won it in 2013.

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In 2014 the White Sox reclaimed the Crosstown Cup after winning the first 3 games of their four-game series. They won the first two video games at Wrigley Field 31 in 12 and 41 respectively, returned to U.S. Cellular Field to win 83 prior to getting burnt out in the final video game 125.

From 2013 to 2018 there was no business sponsor. In 2019 the prize was sponsored by the financial holding business Wintrust and was for that reason called the Wintrust Crosstown Cup. Barrett vs. Pierzynski [edit] The competition turned physical on May 20, 2006, when a brawl broke out during a White Sox-Cubs game at U.S.