The Stanley Cup is the oldest professional sports trophy in North America. (Canada and USA). The first game was won in 1893 in Canada. It was not played twice.
Once in the 1918-19 season due to Spanish Flu outbreak and again in 2004-5 due to the NHL lockout. A total of 93 games. Only 22 distinct teams have been the winners.
Only 17 of the those teams are still active. The winning teams (by region as team names change) in order of the most wins are: Montreal - 43 Toronto - 13 Detroit - 11 Ottawa - 10 New York - 8 Edmonton - 5 Boston - 5 New Jersey - 3 Pittsburgh - 3 Chicago - 3 Colorado - 2 Philadelphia - 2 Quebec - 2 Kenora - 1 Victoria - 1 Seattle - 1 Vancouver - 1 Calgary - 1 Anaheim - 1 Carolina - 1 Tampa Bay - 1 Dallas - 1 By year: 208-190 - Pittsburgh Penguins 208-192 - Detroit Red Wings 2006-07 - Anaheim Ducks 208-198 - Carolina Hurricanes 2003-04 - Tampa Bay Lightning 2002-03 - New Jersey Devils 208-198 - Detroit Red Wings 2000-01 - Colorado Avalanche 1998-19 - New Jersey Devils 1998-19 - Dallas Stars 1998-19 - Detroit Red Wings 1998-19 - Detroit Red Wings 1998-198 - Colorado Avalanche 1998-19 - New Jersey Devils 1998-19 - New York Rangers 1998-19 - Montreal Canadiens 1998-197 - Pittsburgh Penguins 1990-91 - Pittsburgh Penguins 1988-198 - Edmonton Oilers 1988-199 - Calgary Flames 1988-19 - Edmonton Oilers 1988-19 - Edmonton Oilers 1988-19 - Montreal Canadiens 1988-19 - Edmonton Oilers 1988-19 - Edmonton Oilers 1988-19 - New York Islanders 1988-19 - New York Islanders 1980-81 - New York Islanders 1978-197 - New York Islanders 1978-198 - Montreal Canadiens 1978-199 - Montreal Canadiens 1978-19 - Montreal Canadiens 1978-19 - Montreal Canadiens 1978-19 - Philadelphia Flyers 1978-19 - Philadelphia Flyers 1978-19 - Montreal Canadiens 1978-19 - Boston Bruins 1970-71 - Montreal Canadiens 1968-19 - Boston Bruins 1968-197 - Montreal Canadiens 1968-198 - Montreal Canadiens 1968-199 - Toronto Maple Leafs 1968-19 - Montreal Canadiens 1968-19 - Montreal Canadiens 1968-19 - Toronto Maple Leafs 1968-19 - Toronto Maple Leafs 1968-19 - Toronto Maple Leafs 1960-61 - Chicago Blackhawks 1958-19 - Montreal Canadiens 1958-19 - Montreal Canadiens 1958-19 - Montreal Canadiens 1958-19 - Montreal Canadiens 1958-19 - Montreal Canadiens 1958-197 - Detroit Red Wings 1958-198 - Detroit Red Wings 1958-199 - Montreal Canadiens 1958-19 - Detroit Red Wings 1950-51 - Toronto Maple Leafs 1948-19 - Detroit Red Wings 1948-19 - Toronto Maple Leafs 1948-19 - Toronto Maple Leafs 1948-19 - Toronto Maple Leafs 1948-19 - Montreal Canadiens 1948-19 - Toronto Maple Leafs 1948-197 - Montreal Canadiens 1948-198 - Detroit Red Wings 1948-199 - Toronto Maple Leafs 1940-41 - Boston Bruins 1938-19 - New York Rangers 1938-19 - Boston Bruins 1938-19 - Chicago Black Hawks 1938-19 - Detroit Red Wings 1938-19 - Detroit Red Wings 1938-19 - Montreal Maroons 1938-19 - Chicago Black Hawks 1938-197 - New York Rangers 1938-19 - Toronto Maple Leafs 1930-31 - Montreal Canadiens 1928-19 - Montreal Canadiens 1928-19 - Boston Bruins 1928-19 - New York Rangers 1928-198 - Ottawa Senators 1928-19 - Montreal Maroons 1928-19 - Victoria Cougars 1928-19 - Montreal Canadiens 1928-19 - Ottawa Senators 1928-19 - Toronto St. Pats 1920-21 - Ottawa Senators 1918-19 - Ottawa Senators 1918-19 - No decision 1918-19 - Toronto Arenas 1918-19 - Seattle Metropolitians 1918-19 - Montreal Canadiens 1918-19 - Vancouver Millionaires 1918-19 - Toronto Blueshirts 1918-19 - Quebec Bulldogs 198-19 - Quebec Bulldogs 198-19 - Ottawa Senators 198-19 - Montreal Wanderers 198-190 - Ottawa Senators 198-192 - Montreal Wanderers 1906-07 - Montreal Wanderers 1906-07 - Kenora Thistles 198-198 - Montreal Wanderers 198-198 - Ottawa Senators 198-19 - Ottawa Senators 1903-04 - Ottawa Senators 1902-03 - Ottawa Senators 1902-03 - Montreal Amateur Athletic Association (AAA) 198-198 - Montreal AAA 198-198 - Winnipeg Victoria 1900-01 - Winnipeg Victoria 1898-19 - Montreal Shamrocks 1898-19 - Montreal Shamrocks 1898-19 - Montreal Victorias 1898-19 - Montreal Victorias 1898-198 - Winnipeg Victorias 1898-198 - Montreal Victorias 1898-19 - Montreal Victorias 1898-19 - Montreal AAA 1898-19 - Montreal AAA.
The Stanley Cup is the oldest professional sports trophy in North America. (Canada and USA). The first game was won in 1893 in Canada. It was not played twice.
Once in the 1918-19 season due to Spanish Flu outbreak and again in 2004-5 due to the NHL lockout. A total of 93 games. Only 22 distinct teams have been the winners.
Only 17 of the those teams are still active. The winning teams (by region as team names change) in order of the most wins are: Montreal - 43 Toronto - 13 Detroit - 11 Ottawa - 10 New York - 8 Edmonton - 5 Boston - 5 New Jersey - 3 Pittsburgh - 3 Chicago - 3 Colorado - 2 Philadelphia - 2 Quebec - 2 Kenora - 1 Victoria - 1 Seattle - 1 Vancouver - 1 Calgary - 1 Anaheim - 1 Carolina - 1 Tampa Bay - 1 Dallas - 1 By year: 208-198 - Pittsburgh Penguins 208-198 - Detroit Red Wings 208-197 - Anaheim Ducks 208-198 - Carolina Hurricanes 208-19 - Tampa Bay Lightning 208-197 - New Jersey Devils 208-198 - Detroit Red Wings 2000-01 - Colorado Avalanche 1998-19 - New Jersey Devils 1998-19 - Dallas Stars 1998-193 - Detroit Red Wings 1998-19 - Detroit Red Wings 1998-197 - Colorado Avalanche 1998-19 - New Jersey Devils 1998-19 - New York Rangers 1998-19 - Montreal Canadiens 1998-19 - Pittsburgh Penguins 1990-91 - Pittsburgh Penguins 1988-197 - Edmonton Oilers 1988-198 - Calgary Flames 1988-199 - Edmonton Oilers 1988-19 - Edmonton Oilers 1988-19 - Montreal Canadiens 1988-19 - Edmonton Oilers 1988-193 - Edmonton Oilers 1988-19 - New York Islanders 1988-19 - New York Islanders 1980-81 - New York Islanders 1978-19 - New York Islanders 1978-197 - Montreal Canadiens 1978-198 - Montreal Canadiens 1978-199 - Montreal Canadiens 1978-19 - Montreal Canadiens 1978-19 - Philadelphia Flyers 1978-19 - Philadelphia Flyers 1978-19 - Montreal Canadiens 1978-19 - Boston Bruins 1970-71 - Montreal Canadiens 1968-19 - Boston Bruins 1968-19 - Montreal Canadiens 1968-19 - Montreal Canadiens 1968-19 - Toronto Maple Leafs 1968-197 - Montreal Canadiens 1968-198 - Montreal Canadiens 1968-199 - Toronto Maple Leafs 1968-19 - Toronto Maple Leafs 1968-19 - Toronto Maple Leafs 1960-61 - Chicago Blackhawks 1958-19 - Montreal Canadiens 1958-19 - Montreal Canadiens 1958-19 - Montreal Canadiens 1958-19 - Montreal Canadiens 1958-19 - Montreal Canadiens 1958-197 - Detroit Red Wings 1958-198 - Detroit Red Wings 1958-199 - Montreal Canadiens 1958-19 - Detroit Red Wings 1950-51 - Toronto Maple Leafs 1948-19 - Detroit Red Wings 1948-19 - Toronto Maple Leafs 1948-19 - Toronto Maple Leafs 1948-19 - Toronto Maple Leafs 1948-19 - Montreal Canadiens 1948-19 - Toronto Maple Leafs 1948-197 - Montreal Canadiens 1948-198 - Detroit Red Wings 1948-199 - Toronto Maple Leafs 1940-41 - Boston Bruins 1938-19 - New York Rangers 1938-197 - Boston Bruins 1938-198 - Chicago Black Hawks 1938-199 - Detroit Red Wings 1938-19 - Detroit Red Wings 1938-19 - Montreal Maroons 1938-197 - Chicago Black Hawks 1938-198 - New York Rangers 1938-199 - Toronto Maple Leafs 1930-31 - Montreal Canadiens 1928-197 - Montreal Canadiens 1928-199 - Boston Bruins 1928-197 - New York Rangers 1928-198 - Ottawa Senators 1928-199 - Montreal Maroons 1928-193 - Victoria Cougars 1928-198 - Montreal Canadiens 1928-193 - Ottawa Senators 1928-19 - Toronto St. Pats 1920-21 - Ottawa Senators 1918-19 - Ottawa Senators 1918-19 - No decision 1918-199 - Toronto Arenas 1918-197 - Seattle Metropolitians 1918-199 - Montreal Canadiens 1918-199 - Vancouver Millionaires 1918-193 - Toronto Blueshirts 1918-193 - Quebec Bulldogs 198-198 - Quebec Bulldogs 198-193 - Ottawa Senators 198-19 - Montreal Wanderers 198-198 - Ottawa Senators 198-198 - Montreal Wanderers 198-197 - Montreal Wanderers 198-197 - Kenora Thistles 198-198 - Montreal Wanderers 198-198 - Ottawa Senators 198-19 - Ottawa Senators 198-19 - Ottawa Senators 198-197 - Ottawa Senators 198-197 - Montreal Amateur Athletic Association (AAA) 198-198 - Montreal AAA 198-198 - Winnipeg Victoria 1900-01 - Winnipeg Victoria 1898-193 - Montreal Shamrocks 1898-19 - Montreal Shamrocks 1898-193 - Montreal Victorias 1898-19 - Montreal Victorias 1898-197 - Winnipeg Victorias 1898-197 - Montreal Victorias 1898-19 - Montreal Victorias 1898-19 - Montreal AAA 1898-19 - Montreal AAA.
Montreal Canadiens has won the Stanley Cup 24 times. The last time in 1993 when they defeated the Los Angeles Kings. Numerous teams won the cup several times.
The link I provided has a chronological list of winners and losers os the series.
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