The 1959 Stanley Cup Final was contested by the defending champion Montreal Canadiens and the Toronto Maple Leafs. Montreal was making its ninth consecutive appearance in the Final series. It was Toronto's first appearance since 1951. The Canadiens would win the series four games to one to win their fourth-straight Cup victory.
Montreal defeated the Chicago Black Hawks 4–2 to reach the finals. Toronto defeated the Boston Bruins 4–3 to reach the finals.
Rocket Richard, hampered by injuries, did not score at all during the playoffs. Toronto was making its first finals appearance since 1951.
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