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1997
After numerous charity and exhibition games, the WhiteSox and Cubs played for real for the first time in the regular season.
The overall record between the two franchises through the end of the 2002 spring training season had the Sox ahead, 137-91-6, including an amazing 10-0-2 in the “Crosstown Classic” played for charity from 1985-95.
Since then, the two teams have played each other every season multiple times. Going into 2021 the Sox have a 64-60 advantage in regular season interleague meetings.