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Between the 1959-60 and 1968-69 seasons, the Montreal Canadiens had the most series wins by a team in the Stanley Cup Finals, with 5 wins.

which nhl hockey team has won the most stanley cups in the 60's
CanadiensMaple LeafsBlack Hawks541
TEAMSERIES WSERIESGPWLTPTSPTS%GGADIFFPP%PK%S/GPS%SA/GPSV%
CanadiensCanadiens5Stanley Cup Finals31229044.71090583234.198.528.45.934
Maple LeafsMaple Leafs4Stanley Cup Finals281612032.5717973633.618.435.07.926
Black HawksBlack Hawks1Stanley Cup Finals19910018.4744648-228.008.631.84.921

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