The Stanley Cup was first presented to the Montreal Hockey Club in 1893.
Though the Montreal AAA's were the first team to win the stanley cup this was back when the NHL did not exist and multiple leagues could contest for the cups.
The first team to win the cup after the NHL was formed were the Toronto Maple Leafs (Toronto Arenas back then) in 1918
The Toronto Arenas
The Calgary Flames won the Stanley Cup in 1989.
Dick Carroll was the coach of the Leafs when they won the Stanley Cup in the inaugural season of the NHL
The Dallas Stars won the Stanley cup that year in 1998-1999.
The Detroit Red Wings won the Stanley Cup in 1997.
7 Teams have won the Stanley Cup since the Presidents trophy was incorporated in the NHL in 1976.
Chris Chelios is the oldest active NHL player who has not won a Stanley Cup. Chelios plays for the Detroit Red Wings.
The Montreal Canadiens
if you win the championship playoff series in the NHL
18 of them.