April 7, 1994 - In the annual “Crosstown Classic” charity game between the Sox and Cubs, Michael Jordan writes his name into Sox lore. His double in the late innings ties the game and prevents the Sox from losing for the first time in this series. The game would end in a tie. The Sox would go 10-0-2 in this affair that lasted from 1985 through 1995. (Two games were played in 1995)
April 23, 1990 - It was an unusual event even though it happened in an exhibition game. Utility player Steve “Psycho” Lyons played all nine positions for the Sox during the annual “Crosstown Classic” game against the Cubs at Wrigley Field. Manager Jeff Torborg moved him all over the field during the contest won by the Sox 6-5.
April 29, 1985 - A new yearly tradition is established in the first annual "Crosstown Classic" charity game matching the Sox and Cubs. Down through the years both teams played each other on and off in spring training or during an open date in the regular season. This is the first time both teams agreed to play on a yearly basis with a corporate sponsor (Busch Beer). The game alternated between Comiskey Park and Wrigley Field and was played every year through 1995 (Because of the labor impasse the teams played two games that season.) The Sox won the opener at Comiskey Park 7-4 but it’s only the start of a remarkable run.
The two teams played a total of 12 games and the Sox never lost!!!!! They’d go 10-0-2 during that time period. After 1995, the series was dropped. It’s never publicly explained why, but reports persisted that the cancellation of the series was at the Cubs request.
June 16, 1997 - After numerous charity and exhibition games, the Sox and Cubs play for real for the first time in the regular season. The overall record 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 through 1995 (there were two games in 1995.)
June 25, 1964 - An overflow crowd of over 52 thousand, jam Comiskey Park to watch the Sox hammer the Cubs 11-1 in the annual ‘Boys Benefit Game’. What’s significant however is the fact that fans were allowed on the outfield grass behind ropes, since there wasn’t any room left in the park. It’s the last time fans have ever been permitted to stand on the playing field for a game.