Roy retires with several milestones to his credit. He was the member of four Stanley Cup teams: 1986 and 1993 with Montreal, and 1996 and 2001 with Colorado. Along with the Cups, he was awarded the Conn Smythe Trophy (playoff MVP) in three of those four years: 1986, 1993, and 2001. He is the only NHL goaltender with more than 60,000 minutes played, and is also the career leader in games (1,029), wins (551) and playoff wins (151).

He popularized the "butterfly" style of goaltending in the NHL and has spawned an entire generation of students and followers. Both goaltenders in this year's Stanley Cup Finals, Martin Brodeur of New Jersey and Jean-Sebastien Giguere of Anaheim, are Roy disciples, as is Patrick Lalime of Ottawa, whose team reached the conference finals only to be eliminated by New Jersey.

Though he matches up well historically, Roy did not fare well head-to-head with his two largest adversaries, Dominik Hasek and Eddie Belfour. The battle with Hasek was largely statistical, for by the time Hasek reached his peak form with Buffalo, Roy had already moved to the Western conference, and scheduling meant the two rarely faced each other. In their only playoff meeting, last year's conference final between Colorado and Detroit, Roy allowed six goals in a 7-0 game seven loss. Detroit went on to win the Cup and Hasek retired.

Belfour is a different story. While Colorado and Detroit had a bitter rivalry in the middle of the 1990s, the emergence of the Dallas Stars gave each team a new worthy opponent. Belfour eliminated Roy in the 1999 Western Conference finals on his way to the Cup, and again in 2000 before losing to New Jersey in the finals. Colorado did not face Dallas on the way to its 2001 Stanley Cup.