<Ul> <Li> ← 1966 </Li> <Li> Stanley Cup Finals </Li> <Li> 1968 → </Li> </Ul> <Li> Stanley Cup Finals </Li> <P> The 1967 Stanley Cup Finals was a best - of - seven series played between the Montreal Canadiens and the Toronto Maple Leafs . The Maple Leafs ended up winning the series, four games to two . In doing this, they won their thirteenth Stanley Cup . To date, this is Toronto's most recent Stanley Cup championship, most recent appearance in the championship final, and is tied for the longest - active championship drought in the NHL with the St. Louis Blues (who have never won since joining the NHL in 1967) at 49 (not including 2004--05 lockout) seasons . The 1967 Stanley Cup Final was also the last Stanley Cup Final in the Original Six Era . </P> <P> This was the last Stanley Cup before the 1967 expansion which meant there were only two rounds and three series in total were played in the playoffs . Montreal defeated New York to advance to the finals and Toronto defeated Chicago . </P>

When was the last time toronto won the stanley cup