11 times
They have been to the Stanley Cup finals 4 times and countless playoffs.
The St. Louis Blues have been to the Stanley Cup Finals three times, 1968, 1969 and 1970.
The Montreal Canadiens who have won the Stanley Cup 24 times!
Three so far.
The Toronto Maple Leafs have lost in the Stanley Cup Finals 8 times. Both the Montreal Canadiens and the Philadelphia Flyers have lost 6 times.
7 of them.
4
This (2011) is the first time the two teams have met in the finals. The Canucks have been to the finals twice before: in 1982 and in 1994. The Bruins have been to the finals seven times before, most recently in 1990.
The Flyers have been in the playoffs a total of 34 times in their 42 year history. They have reached the Stanley Cup Finals a total of 8 times (73-74*, 74-75*, '75-76, '79-80, '86-87, '96-97, 2009-'10) While they have been in the Stanley Cup Finals 8 times, they only have 7 Conference Championships, as in their first Stanley Cup Finals appearance, there was no Conference Championship Title. * = Won the Stanley Cup
3 times: 1986, 1989 (win), and 2004. Additionally the 1924 Calgary Tigers of the WCHL lost while playing the Montreal Canadiens for the Stanley Cup.
They've been to the finals once, in 1998.
The Vancouver Canucks playoff history has had its ups and downs. In the 22 times they have made the playoffs, the team has won 12 playoff series. Their first ever playoff appearance was in 1975, after receiving a first round bye for winning their division the Canucks faced the Montreal Canadians. The ninth seeded Canucks were beaten in five by the Canadiens.