Marian Hossa 3 finals in 3 consecutive years with 3 three different teams. Plays for the Pens in 07-08 against the Wings and loses. Plays for the Wings in 08-09 against the Pens and loses. Finally wins it with the Hawks the next year
Even if we take Henri Richard's Cup final losses, it still only adds up to 1 and that was 1967. The Canadiens lost in the final in 1955 to Detroit and did not lose in the final until 1967, and then until 1989 again.
Propp is one of the correct answers here. He went 0-5 in the Cup final. Norm Ullman has the same record too. Brad Park is 0-3 and that doesn't include 1979 which to many people was the Cup final that year.
As for goalies I guess Tony Esposito technically went 0-2. He did win a Cup as a third string goalie in 1969 with Montreal but didn't play a playoff game. Is there another goalie that went 0-2 or worse?
They've won it before obviously but the Flyers have lost 6 straight Finals in a row. Anybody have a longer streak than that going?
If you count the Canucks as a continuation of the WWI era Millionaires franchise, than Vancouver has lost 6 Stanley Cup finals since their last win in 1915 (1918, 1921, 1922, 1982, 1994, 2011).
To make matters worse, 5 of those losses came in a deciding game. Seven times a Vancouver team has gone into a game just needing a win to win the Stanley Cup, and seven times they have lost, and they've scored just 7 goals in those 7 games. They've been unfortunate enough to be facing a Hall of Fame defenceman every single time they go to the finals.