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Sidney Crosby has won the Stanley cup once, in 2009. He became the youngest captain to win the Stanley Cup, just under 22 years of age.

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Wiki User

11y ago
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4 times

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Wiki User

13y ago
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ZERO

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Wiki User

15y ago
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2

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Wiki User

12y ago
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Q: How many times has Sidney Crosby won the Stanley Cup?
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