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[Has there] ever been a team who has not lost a game during the NHL playoffs to win the [Stanley] cup?

Since 1939 (the first best-of-seven Stanley Cup finals), this has taken place only twice, albeit during the era in which there were only six teams in the league (and two playoff rounds).

• 1960 - Montreal Canadiens

• 1952 - Detroit Red Wings

Between 1926-1938, this took place five times:

• 1930 - Montreal Canadiens
• 1929 - Boston Bruins
• 1927 - Ottawa Senators
• 1926, 1935 - Montreal Maroons

Since 1939 (the first best-of-seven Stanley Cup finals), the following teams lost only once on their way to the Stanley Cup:

• 1948, 1949 - Toronto Maple Leafs
• 1944, 1946, 1968 _†, 1976 _‡ - Montreal Canadiens

_{† - 12 teams in the league (three playoff rounds)
‡ - 18 teams in the league (three playoff rounds, division winners earned a bye to the quarterfinals)}

Between 1926-1938, the following teams lost only once on their way to the Stanley Cup:

• 1936 - Detroit Red Wings

• 1934 - Chicago Black Hawks

• 1933 - New York Rangers

• 1932 - Toronto Maple Leafs

[Has there] ever been a team who has not lost a game during the NHL playoffs to win the [Stanley] cup?

Since 1939 (the first best-of-seven Stanley Cup finals), this has taken place only twice, albeit during the era in which there were only six teams in the league (and two playoff rounds).

• 1960 - Montreal Canadiens

• 1952 - Detroit Red Wings

Between 1926-1938, this took place five times:

• 1930 - Montreal Canadiens
• 1929 - Boston Bruins
• 1927 - Ottawa Senators
• 1926, 1935 - Montreal Maroons

Since 1939 (the first best-of-seven Stanley Cup finals), the following teams lost only once on their way to the Stanley Cup:

• 1948, 1949 - Toronto Maple Leafs
• 1944, 1946, 1968 _†, 1976 _‡ - Montreal Canadiens

_{† - 12 teams in the league (three playoff rounds)
‡ - 18 teams in the league (three playoff rounds, division winners earned a bye to the quarterfinals)}

Between 1926-1938, the following teams lost only once on their way to the Stanley Cup:

• 1936 - Detroit Red Wings

• 1934 - Chicago Black Hawks

• 1933 - New York Rangers

• 1932 - Toronto Maple Leafs

[Has there] ever been a team who has not lost a game during the NHL playoffs to win the [Stanley] cup?

Since 1941 (the first time a Stanley Cup finals sweep took place according to this answer), this has taken place only twice, albeit during the era in which there were only six teams in the league (and two playoff rounds).

• 1960 - Montreal Canadiens

• 1952 - Detroit Red Wings

Between 1926-1941, this took place five times:

• 1930 - Montreal Canadiens
• 1929 - Boston Bruins
• 1927 - Ottawa Senators
• 1926, 1935 - Montreal Maroons

Since 1941, the following teams lost only once on their way to the Stanley Cup:

• 1948, 1949 - Toronto Maple Leafs
• 1944, 1946, 1968 _†, 1976 _‡ - Montreal Canadiens

_{† - 12 teams in the league (three playoff rounds)
‡ - 18 teams in the league (three playoff rounds, division winners earned a bye to the quarterfinals)}

Between 1926-1941, the following teams lost only once on their way to the Stanley Cup:

• 1936 - Detroit Red Wings

• 1934 - Chicago Black Hawks

• 1933 - New York Rangers

• 1932 - Toronto Maple Leafs

[Has there] ever been a team who has not lost a game during the NHL playoffs to win the [Stanley] cup?

Since 1939 (the first best-of-seven Stanley Cup finals), this has taken place only twice, albeit during the era in which there were only six teams in the league (and two playoff rounds).

• 1960 - Montreal Canadiens

• 1952 - Detroit Red Wings

Between 1926-1938, this took place five times:

• 1930 - Montreal Canadiens
• 1929 - Boston Bruins
• 1927 - Ottawa Senators
• 1926, 1935 - Montreal Maroons

Since 1939 (the first best-of-seven Stanley Cup finals), the following teams lost only once on their way to the Stanley Cup:

• 1948, 1949 - Toronto Maple Leafs
• 1944, 1946, 1968 _†, 1976 _‡ - Montreal Canadiens

_{† - 12 teams in the league (three playoff rounds)
‡ - 18 teams in the league (three playoff rounds, division winners earned a bye to the quarterfinals)}

Between 1926-1938, the following teams lost only once on their way to the Stanley Cup:

• 1936 - Detroit Red Wings

• 1934 - Chicago Black Hawks

• 1933 - New York Rangers

• 1932 - Toronto Maple Leafs

[Has there] ever been a team who has not lost a game during the NHL playoffs to win the [Stanley] cup?

Since 1941, this has taken place only twice, albeit during the era in which there were only six teams in the league (and two playoff rounds).

• 1960 - Montreal Canadiens

• 1952 - Detroit Red Wings

Between 1926-1941, this took place five times:

• 1930 - Montreal Canadiens
• 1929 - Boston Bruins
• 1927 - Ottawa Senators
• 1926, 1935 - Montreal Maroons

Since 1941, the following teams lost only once on their way to the Stanley Cup:

• 1948, 1949 - Toronto Maple Leafs
• 1944, 1946, 1968 _†, 1976 _‡ - Montreal Canadiens

_{† - 12 teams in the league (three playoff rounds)
‡ - 18 teams in the league (three playoff rounds, division winners earned a bye to the quarterfinals)}

Between 1926-1941, the following teams lost only once on their way to the Stanley Cup:

• 1936 - Detroit Red Wings

• 1934 - Chicago Black Hawks

• 1933 - New York Rangers

• 1932 - Toronto Maple Leafs

[Has there] ever been a team who has not lost a game during the NHL playoffs to win the [Stanley] cup?

Since 1941 (the first time a Stanley Cup finals sweep took place according to this answer), this has taken place only twice, albeit during the era in which there were only six teams in the league (and two playoff rounds).

• 1960 - Montreal Canadiens

• 1952 - Detroit Red Wings

Between 1926-1941, this took place five times:

• 1930 - Montreal Canadiens
• 1929 - Boston Bruins
• 1927 - Ottawa Senators
• 1926, 1935 - Montreal Maroons

Since 1941, the following teams lost only once on their way to the Stanley Cup:

• 1948, 1949 - Toronto Maple Leafs
• 1944, 1946, 1968 _†, 1976 _‡ - Montreal Canadiens

_{† - 12 teams in the league (three playoff rounds)
‡ - 18 teams in the league (three playoff rounds, division winners earned a bye to the quarterfinals)}

Between 1926-1941, the following teams lost only once on their way to the Stanley Cup:

• 1936 - Detroit Red Wings

• 1934 - Chicago Black Hawks

• 1933 - New York Rangers

• 1932 - Toronto Maple Leafs