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 Torontos
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Victoria cougars
The inaugural Stanley Cup was Awarded to the Montreal Amateur Athletic Association in 1893. The Victoria Cougars became the last non-NHL team to win the Cup in 1925, but they were definitely not the first.
The very first Stanley Cup winner was the Montreal Amateur Athletic Association. Montreal AAA for short. They were also known as the Montreal Hockey Club. They won in 1893. They were awarded the Cup as they were the AHAC champions. In 1894, they beat the Ottawa HC.
The first team to win the Stanley Cup when NHL teams were able to win the Cup was the Toronto Arenas in 1917 against the Vancouver Millionaires (PCHA).
The first team to win the Stanley Cup when the NHL teams only competed for the Cup was the Ottawa Senators against the Boston Bruins in 1927
The Montreal AAA in 1893. the Toronto arenas ( later the st.pats and then the maple leafs) were the first team to do it in the nhl in 1918.