The oldest person to ever win a Stanley Cup as a player was Chris Chelios. He was 46 years and 5 months old when he won it as a member of the Detroit Red Wings in June of 2008. Complete list of Stanley Cup Winners.
Born on January 25, 1962 in Chicago, Chelios began his NHL career with the Montreal Canadiens in 1983. He also played for the Chicago Blackhawks, Detroit Red Wings, and a few games for the Atlanta Thrashers before retiring after the 2009-10 season. Chelios played 1,651 regular season NHL games plus 268 playoff games and scored a total of 216 goals, 876 assists, and racked up 3,314 penalty minutes.
The oldest player to ever score a goal in the Stanley Cup Finals was Mark Recchi of the Boston Bruins on June 6, 2011 against the Vancouver Canucks. Recchi was 43 years, 126 days old at the time of scoring that goal.
The oldest goalie to ever win a Stanley Cup was Dominik Hasek with the Detroit Red Wings in 2008. Although he was mainly the backup goalie to Chris Osgood, Hasek was 43 years and 5 months old when he became a Stanley Cup Champion.
The oldest coach to win a Stanley Cup is Scotty Bowman with the Detroit Red Wings in 2002. It was the 9th Cup for Bowman as a coach and he was 68 years old at the time.