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19 games in 1904 ...........Better answer--> 19 games in 1906. The Sox started that season in 6th place but won that 19 in a row late in the year, putting them into position to win the A.L. Pennant and go on to the World Series against the Chicago Cubs, who they beat 4 games to 2 for the Championship.

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Q: What is the longest winning streak in Chicago White Sox history?
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