Won Stanley Cup
In 1985-86, Roy was one of the two goalies (the other being Brian Hayward) carried by the Canadiens during the regular season. He posted a respectable regular-season record of 23-18-3 with goals against of 3.35, and carried much of the load during the playoffs. Though a rookie, Roy played like a veteran. During the playoffs, he had a record of 15-5 with a 1.92 goals against average. Montreal defeated the Calgary Flames to win the Stanley Cup. Roy was named playoff MVP, the youngest player to ever win the honor. He made $80,000 for the season. Roy was one of the keys to Montreal's success, but he also had a great defense in front of him. He was still developing his butterfly style of play. He had some flaws in his style, included angles and puck handling, but corrected them. It was also revealed that Roy had some goalie quirks, including that he talked to his goalposts telling them they will all play well and no pucks will go in.
Describing his goaltending style, Robin Finn of the New York Times wrote, "the lanky Roy shimmies and shivers in his crease like a twitching stork. While his positioning is usually impeccable, he rarely remains statuesque for long, and tends to flail his way to the ice in pursuit of rebounds."
Roy could not immediately follow-up this success. In 1987 and 1988, he put much pressure on himself to repeat with the Stanley Cup, instead of focusing on winning in the first round of the playoffs. Though he was nominated for the Vezina Trophy, the award given to the best goalie in the NHL, he had more improvement in 1988-89 as he became more consistent in the regular season.
Roy finally won his first the Vezina Trophy in 1989, a year in which he lead the league with a 2.47 goals against average. He also won the Vezina in 1990 and 1992. In 1991-92, Roy lead the league with a 2.36 goals against average, but the Canadiens lost in the second round to the Boston Bruins.