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.
According to NHL.com's Stanley Cup Record Book & History web page, Scotty Bowman has won more Stanley Cups than any other coach with a total of 9 championships. One more than Toe Blake who won 8 Cups as a coach. Contributed by Kevin H. Bugg, DC " Go Leafs! "
Scotty Bowman won 3 Stanley Cups with the Detroit Red Wings, in 1997, 1998, and 2002.
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
The Montreal Canadiens (Correct Spelling) Have Won 24 stanley cups