• Saturday, July 23, 2016

    What player has won the most Stanley Cups?

    Henri Richard holds the record for playing on the most Stanley Cup champions, winning 11 times in his career. During Richard's 20 years with the Montreal Canadiens from 1955- 56 to 1974-75, "The Pocket Rocket" never played more than four consecutive seasons without earning a new Stanley Cup ring.Henri Richard holds the record for playing on the most Stanley Cup champions, winning 11 times in his career. During Richard's 20 years with the Montreal Canadiens from 1955- 56 to 1974-75, "The Pocket Rocket" never played more than four consecutive seasons without earning a new Stanley Cup ring.