Which NHL team has won the most consecutive Stanley Cups? The Montreal Canadiens have won the Stanley Cup 24 times, the most of any team. They also won the most in a row: five between 1955-56 and 1959-60. Henri Richard of the Montreal Canadiens appears the most on the Stanley Cup, 11 times.
How many NHL teams have won three consecutive Stanley Cups? Just three separate teams – the New York Islanders, Toronto Maple Leafs and Montreal Canadiens – have won the Stanley Cup three times in a row, with Montreal and Toronto accomplishing the task twice.
Has any team won 6 Stanley Cups in a row? Tampa Bay is the first team to win consecutive championships since the Pittsburgh Penguins in 2016 and 2017.
Has any NHL team won 5 Stanley Cups in a row? On April 14, 1960, the Montreal Canadiens defeat the Toronto Maple Leafs to win the Stanley Cup for a record fifth year in a row.