Through the 2009 season, once.
That was the 1917 season when the White Sox went 100-54 and defeated the New York Giants in the World Series.
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Steve Carlton played for the Chicago White Sox in 1986, he wore #32 and #37 during that season.
Larry Doby was traded by the Cleveland Indians to the Chicago White Sox during the 1949 season. Doby appeared in 14 games for the American League champion White Sox toward the end of that season, but was not on their post-season roster and did not play in the World Series that year. He retired at the end of the season at age 35.
Through the 2008 season, the last season both the Cubs and White Sox were in the MLB playoffs was 1906. The White Sox defeated the Cubs, 4 games to 2, in the World Series. This is the only season both Chicago teams made the MLB playoffs in the same season.
Wilbur Wood of the Chicago White Sox was 24-20 during the 1973 season, making him the last pitcher in American League history to win and lose 20 or more games in the same season.
Joe Jackson of the Chicago White Sox in 1920.