Which Players Have Won the Most Stanley Cups?

You won’t be surprised to learn that seven of the eight players with the most Stanley Cups achieved all of their success with the Montreal Canadiens. 

The player with the most Stanley Cups played for the Canadiens in 11 of their 24 Stanley Cup triumphs. 

Which Players Have Won the Most Stanley Cups? 

Glenn Anderson, who won six Stanley Cups – five with the Edmonton Oilers and one with the New York Rangers – is the player among the top 10 who most recently celebrated his titles. 

The Oilers were perennial Stanley Cup odds front-runners during the mid-to-late 1980s.

8. Serge Savard (8 Cups)

Serge Savard won eight Stanley Cups with the Canadiens in 11 years, from 1968 to 1979. He also won the Conn Smythe Trophy in 1969, thanks to scoring 10 points (four goals, six assists) in 14 games. 

7. Maurice Richard (8 Cups)

Maurice Richard, after whom the Rocket Richard Trophy is named, won eight Cups with the Habs from 1944 to 1960. 

He won five in a row from 1956 to 1960. All of his Stanley Cup triumphs came before the Conn Smythe Trophy was introduced in 1965.

6. Jacques Lemaire (8 Cups)

Jacques Lemaire won eight Stanley Cups in just 12 NHL seasons from 1967-68 to 1978-79. All of his Cups came with the Canadiens, and he was among those with the most playoff games by a Canadiens player.

5. Red Kelly (8 Cups)

Red Kelly played for 20 years and won eight Stanley Cups. He won four with the Detroit Red Wings and four with the Toronto Maple Leafs, setting him apart from the others on the list. 

He was part of the Maple Leafs’ three-peat from 1961 to 1964. 

4. Claude Provost (9 Cups)

Claude Provost won nine Stanley Cups in 14 trips to the postseason. He was part of the Habs team that won five straight. 

His nine Cups occurred over 13 years, and he won his first in 1956, his rookie season. 

3. Yvan Cournoyer (10 Cups)

Remarkably, Yvan Cournoyer celebrated 10 championships in just 12 trips to the playoffs. He was only in the NHL for 16 years, from 1963 to 1979. 

He left an indelible mark for countless reasons, including being among the Canadiens with the most game-winning goals in the playoffs.

2. Jean Beliveau (10 Cups)

Jean Beliveau played in the NHL for 21 years, including 17 playoff appearances, all with the Canadiens. Rewarded with 10 Stanley Cups, Beliveau won the first edition of the Conn Smythe in 1965.

1. Henri Richard (11 Cups)

Henri Richard won 11 Stanley Cups in his 20 seasons with the Canadiens, a record that will likely never be surpassed. 

He won five in a row to start his career and six in a nine-year span (1965 to 1973) toward the end.