23
Ken Dryden won 6 Stanley Cups in a career that only spanned 8 years.
The Canadians
Bowman won 9 Stanley Cups between 1973 and 2002 as head coach of the Montreal Canadiens (1973, 1976, 1977, 1978, 1979), Pittsburgh Penguins (1992), and Detroit Red Wings (1997, 1998, 2002). He also was a front office member when the Penguins (1991), Red Wings (2008), and Chicago Blackhawks (2010) won Stanley Cups.
Canadiens
ken dryden -6
Montreal Canadians with 24
Toronto
ken dryden
The Montreal Canadiens have won 24, which is the most by far.
Montreal Canadien won this and most Stanley cups.
No, the Montreal Canadiens have won the most Stanley Cups.