Edmonton Oilers - 5 (1984, 1985, 1987, 1988, 1990)
Ken Dryden won 6 Stanley Cups in a career that only spanned 8 years.
Montreals canadians
They have won eleven Stanley cups in there histroy the most recent four are 1997,1998,2002,2008,
The Canadians
Scotty Bowman
Montreal Canadiens - 24 Stanley cups. Last Time, 1993 against the Los Angles kings.
ken dryden
ken dryden -6
Canadiens
Montreal Canadians with 24
Toronto
The Montreal Canadiens have won 24, which is the most by far.