The 1938 Stanley Cup Final was a best-of-five series between the Chicago Black Hawks and the Toronto Maple Leafs. Chicago won the series 3–1 to win their second Stanley Cup. With their record of 14–25–9, they possess as of 2022, the lowest regular season winning percentage (.291) of any championship team in the four major professional sports leagues. They are also the Stanley Cup winning team with the lowest number of Hockey Hall of Fame members as a player, with only one. Won the 1938 Stanley Cup Final on April 12, 1938. Wiki link