Which NHL team has not won the Stanley Cup the longest? With a first-round exit in the 2022 playoffs, the Maple Leafs tied the record for longest Stanley Cup drought in NHL history, matching the New York Rangers’ mark from 1940 to 1994. After the Maple Leafs, the Buffalo Sabres and Vancouver Canucks share the second-longest Cup drought at 51 years.
Who won the Stanley Cup the most? Despite their last championship coming in 1993, the Montreal Canadiens have an extremely comfortable lead for first place among title winners in NHL history. Montreal, an “Original Six” club, has 23 Stanley Cup championships since 1918, which is 11 more than the next-closest team.
Has any NHL team never made the playoffs? The longest currently active NHL Playoffs drought belongs to the Buffalo Sabres, who have gone 11 seasons without making the Playoffs.
Who has lost the Stanley Cup the most? The Boston Bruins have the most series losses by a team in the Stanley Cup Finals, with 14 losses.