NHL Records: The Masters of the Stanley Cup Playoffs
In the high-stakes world of the NHL, the Stanley Cup Playoff schedule is completely different than the regular season. The Stanley Cup is the ultimate goal for any team, but the Conn Smythe Trophy is the gold standard for individual playoff dominance. Named after the legendary Toronto Maple Leafs builder, this trophy has been awarded since 1965 to the player judged most valuable to his team throughout the entire playoff run. Winning it once helps define a career, but winning it multiple times puts a player on a pedestal of peak performance when it matters most.
The Phenomenal Run of Patrick Roy
When discussing the absolute summit of playoff dominance, one name stands alone. Goaltender Patrick Roy is the only player in NHL history to capture the Conn Smythe Trophy three times. What makes this record absolutely amazing is that Roy didn’t just have one extraordinary spring; he backstopped championship runs across three different decades. He first won the award with the Montreal Canadiens in 1986, followed by a second historic performance with Montreal in 1993. He proved his enduring greatness nearly a decade later, winning his third trophy in 2001 after leading the Colorado Avalanche to glory. For a goalie to remain the best on the ice over such a long stretch is a total masterclass in hockey excellence.
The Elite Circle: Two-Time Winners
Outside of “Saint Patrick”, five other legends have managed to climb this mountain more than once. These players represent the gold standard of their eras, and the years they won speak volumes about their consistency under pressure. The first to achieve the feat was the defensive phenom Bobby Orr, who took home the hardware in 1970 and 1972. He was followed by Bernie Parent, who put on a goaltending clinic for the Philadelphia Flyers to win in 1974 and 1975.
As the game changed, more legends joined this club. Wayne Gretzky picked up his two Conn Smythe Trophies in 1985 and 1988 with the Oilers, and Mario Lemieux followed that up by leading the Penguins to back-to-back titles in 1991 and 1992. More recently, Sidney Crosby locked in his legacy with his own consecutive Conn Smythe Trophy wins in 2016 and 2017.
A Legacy of Legendary Playoff Performance
The Conn Smythe isn't a trophy you can just stumble into; it requires a level of grit and talent that few ever reach. In the storied history of the Conn Smythe Trophy, it is absolutely phenomenal that Patrick Roy reached the three-trophy mark, while five other stars secured two. These six NHL stars are the ultimate playoff masters—stars who didn't just play for the Stanley Cup, but defined the very outcome of the four playoff rounds.