The oldest club in the postseason tournament is the New York Islanders (28.9). With that in mind, here are the five youngest goalies ever to start a Stanley Cup Playoffs game: Harry Lumley, Detroit Red Wings (Mar. 7 August 1987) became the youngest captain of a Stanley Cup winning team when the Pittsburgh Penguins (USA) defeated the Detroit Red Wings (USA) in the 2009 finals. Gaye Stewart held the previous record in 1942 at 18 years, 9 months, and 21 days. The Hawks' average age of 25.6 years old led all squads as the youngest, followed by the New York Rangers (25.7). Only 1,134 players have ever been able to etch their name onto the Stanley Cup in the trophyâs 123 year existence. Roughly, that equates to a mere 20% of players to ever play in the league being able to hoist the Stanley Cup. At 21 years 10 months 5 days, Sidney Crosby (Canada, b. Larry Hillman was the youngest to win Stanley Cup, Sidney Crosby the youngest to take the Art Ross Trophy. According to The Hockey Writers, there are over 2,300 names on the cup, and the youngest ⦠Wore #4 for the Boston Bruins (D) Two time Stanley Cup CHampion with the Bruins (1970, 1972) Once had a 7 point game Changed the way defensemen play the game Member of the "100 Greatest Players in the NHL" club In the ⦠Known widely for his leaping Stanley Cup winning goal for the Boston Bruins in 1970 vs the Blues. In the 1955 Stanley Cup Finals, Larry Hillman (Detroit Red Wings) became the youngest player to be engraved on the Stanley Cup at 18 years, 2 months, 9 days. The first winner of the Stanley Cup was the Montreal Amateur Athletic Association (AAA), champions of the Amateur Hockey Association of ⦠Getting his name on the Stanley Cup is an NHL player's dream, but only a select few ever manage to reach that highest of honors. The youngest player to ever win the Cup was Larry Hillman. To put that into perspective, there have been 5, 649 players to lace up their skates in the NHL. Just ask Patrick Roy or Ken Dryden. Getty Images. NHL, the NHL Shield, the word mark and image of the Stanley Cup, the Stanley Cup Playoffs logo, the Stanley Cup Final logo, Center Ice name and logo, NHL Conference logos, NHL Winter Classic name, and The Biggest Assist Happens Off The Ice are registered ⦠In the 1955 Stanley Cup Finals, Larry Hillman (Detroit Red Wings) became the youngest player to be engraved on the Stanley Cup at 18 years, 2 months, 9 days. The Conn Smythe Trophy (French: Trophée Conn Smythe) is awarded annually to the most valuable player (MVP) during the National Hockey League's (NHL) Stanley Cup playoffs.It is named after Conn Smythe, the longtime owner, general manager, and head coach of the Toronto Maple Leafs.The Conn Smythe Trophy has been awarded 53 times to 46 players ⦠On Tuesday, Sportsnet's Chris Johnston shared a list of each club competing in the 24-team postseason's average age. Youngest Player to win the Stanley Cup: Larry Hillman, April 14, 1955 18 years, 68 days (played 2 games in Semi-finals, did not play in the finals) Oldest Player to win the Stanley Cup: Chris Chelios , June 4, 2008, 46 years, 130 days (did not play in 2008 finals, so Doug Harvey keeps record for oldest defenceman to play in finals) NHL.com is the official website of the National Hockey League. He was just 18 years, 2 months, and 9 days old when the Boston Bruins won the cup in 1955.