Many teams have never won the Stanley Cup.
The Stanley cup finals have only went up to 7 games and never past.
27 different teams
18 of the active teams.
13 current NHL teams have not won the Stanley Cup, if the Ottawa Senators are counted. The original Ottawa Senators won numerous Stanley Cups, but the newer expansion team has not. If the Ottawa Senators are not counted, then this number falls to 12.
The Montreal Canadiens have won the Stanley Cup 24 times. If Canadians refers to teams from Canada, The Stanley cup has been won by Canadian teams a total of 51 times, including defunct teams.