Player and coach together : Henry Richard, of the Montréal Canadiens, won the cup 11 times. Hector "toe" Blake won the cup 2 times as a player of the Montréal Canadiens and 8 times as a coach of the Montréal Canadiens for a total of 10 cups. Next, there is Jean Beliveau and Yvan Cournoyer who won the cup 10 times. As a coach, Scotty Bowman has won it nine times.
http://www.legendsofhockey.net/HTML/silver_stFFFs.htm
Henri Richard won the most as a player (11) but Jean Beliveau's name is listed the most times on the cup (18) because he won as both a player and team official. (Posted by a Red Wings fan in Israel)
Scotty Bowman. He has nine Stanley Cups with the Montreal Canadiens, (1973, 1976, 1977, 1978, 1979) Pittsburgh Penguins, (1992) and Detroit Red Wings (1997, 1998, 2002).
Scotty Bowman
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.