The Calgary Flames won the Stanley cup in 1989. They did not make the playoffs in the 2013 season.
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While the Atlanta Flames were relatively successful on the ice, they never won a Stanley Cup. However, the Flames were sold to new owners, moved to Calgary and did win a Cup as the Calgary Flames in the 1988-89 season.
They defeated the Montreal Canadiens.
3 times: 1986, 1989 (win), and 2004. Additionally the 1924 Calgary Tigers of the WCHL lost while playing the Montreal Canadiens for the Stanley Cup.
Yes. They won their first Stanley Cup in 2004.
No, he did not win the Stanley Cup.