The NHL was formed in 1917 and played its first season in 1917/18. The winner of the Stanley Cup was the Toronto team simply known as the Arenas. Two things should be noted here:
1. The Cup was not solely an NHL trophy at that time.The NHL champions, the Toronto team, actually had to win against a team from Vancouver which was not a member of the NHL. 2. The Montreal Canadiens actually won the Cup in 1916 before the NHL was founded so they are not considered to be the first NHL team to win the Cup.
the montrial canadians
The Toronto Arenas
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 1918The Torontos
The Montreal Canadians won the Cup in 1916 but they were not a member of the NHL as the league wasn't founded until the 1917/18 season. The first NHL champions were the Toronto team known as the Arenas. Since the Cup wasn't sole property of the NHL at that time, the Toronto team actually had to beat a team from Vancouver to claim the Stanley Cup.
the Montreal Canadiens
The Calgary Flames won the Stanley Cup in 1989.
The Montreal Canadiens