The first winner of the award was centreJean Béliveau of the Montreal Canadiens in 1965. The first player to win it twice was Bobby Orr, who scored the Cup-clinching goals in 1970 and 1972 en route to his Conn Smythe Trophy wins, and he is the only defencemen to achieve this honor more than once. GoaltenderBernie Parent and centres Wayne Gretzky and Mario Lemieux also won it twice, and goaltender Patrick Roy is the only player who has won it three times, as well as the only player to win the trophy for more than one team; he also won it in three different decades. The only winners of the Conn Smythe Trophy in back to back seasons were Bernie Parent in 1974 and 1975, and Mario Lemieux in 1991 and 1992. 1971 winner Ken Dryden remains the only NHL player to ever win the Conn Smythe Trophy before winning the Calder Trophy as rookie of the year, due to being called up by the Montreal Canadiens and only playing six regular season games, which is not enough to qualify as a rookie season. Dave Keon's eight playoff points in 1967 is the fewest ever by a non-goalie Conn Smythe winner, as he was a defensive forward, and at the present he is the only Toronto Maple Leafs player to win the trophy donated by his club's parent company.
Though the award covers the entirety of the playoffs, it has never been given to a player whose team did not at least reach the final. The trophy has been awarded to members of the team that lost the final five times, the most recent being Jean-Sébastien Giguère of the Mighty Ducks of Anaheim in 2003, who backstopped his team on a surprise run to the Finals where they pushed the New Jersey Devils to seven games. The only non-goaltender to win the award in a losing cause is Philadelphia's Reggie Leach, who won it in 1976 as he had set a league record for most goals in the playoffs (19), which included a five-goal game in the semi-finals and four goals in the Finals series, even though his team was swept by the Canadiens.
As of 2014, the trophy had been won sixteen times each by centres and goaltenders, nine times by defensemen, seven times by right wings, and just once by a left wing (Bob Gainey of Montreal in 1979).