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| firstwinner = [[Montreal Hockey Club]] (4) {{small|([[Amateur Hockey Association of Canada|AHAC]])}}
| mostwins = [[Montreal Canadiens]] (24)<ref group="nb" name="MTL24">The Montreal Canadiens won the Stanley Cup the first time as a member of the [[National Hockey Association]], and the last 23 times as a member of the [[National Hockey League]].</ref>
| mostrecent = [[2023–24
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