Which goaltender was the first to win three Conn Smythe Trophies?

Patrick Roy was the first goaltender to win three Conn Smythe Trophies as the NHL’s playoff MVP.

Roy won his first Conn Smythe in 1986 with the Montreal Canadiens, then captured the award again during Montreal’s 1993 championship. His third came in 2001, when he led the Colorado Avalanche to the Stanley Cup.

The three awards came with two different franchises, demonstrating Roy’s influence across separate stages of his career. He became known for his butterfly style, positioning, and ability to perform under playoff pressure.

Roy’s three Conn Smythe wins remain a goaltending benchmark. The award was first presented in 1965 and is voted on by members of the Professional Hockey Writers Association after the Stanley Cup Final.