Patrick Roy won the Stanley Cup at the age of 20 as a goalie for the Montreal Canadiens in 1986.
I think it is Ladanian Tomlinson
Ilya Nikolayevich Bryzgalov
No, he did not win the Stanley Cup.
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.
At age 21 Sidney Crosby is the youngest captain in NHL history to win the Stanley Cup. Jordan Staal is only 20 and won but I don't know the actual record.
I love Stanley cup and was curious to know a lot about Stanley cup, so collected some good links related to Stanley cup, that answers all the common questions. Check out the related link for the same.