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.
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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).