Tomas Plekanec scored on Montreal's eighth attempt in the shootout to lead the Canadiens to a 3-2 win over the Pittsburgh Penguins on Tuesday night.
Carey Price made 32 saves during regulation and then stopped six of eight Pittsburgh shooters in the tiebreaker, including Jason Williams on the Penguins' final attempt.
Evgeni Malkin used a spin-around move to convert Pittsburgh's second attempt after Rene Bourque shot and scored on Montreal's first.
Montreal's Lars Eller and Pittsburgh's Chris Kunitz both scored in the fifth round.
The Canadiens, who beat Winnipeg 3-0 on Sunday, won for just the second time in nine shootouts this season.