<P> From 1914 to the end of the 2017 season , the trophy has been won 99 times . 23 different teams have won the cup , 18 of which are still active in the NHL . Prior to that , the challenge cup was held by nine different teams . The Montreal Canadiens have won the Stanley Cup 24 times and made the finals an additional ten times . There were two years when the Stanley Cup was not awarded : 1919 , because of the Spanish flu epidemic , and 2005 , because of the NHL lockout . </P>
<P> From 1914 to the end of the 2017 season , the trophy has been won 99 times . 23 different teams have won the cup , 18 of which are still active in the NHL . Prior to that , the challenge cup was held by nine different teams . The Montreal Canadiens have won the Stanley Cup 24 times and made the finals an additional ten times . There were two years when the Stanley Cup was not awarded : 1919 , because of the Spanish flu epidemic , and 2005 , because of the NHL lockout . </P>
who 's won the stanley cup the most
who 's won the stanley cup the most
Montreal Canadiens
Montreal Canadiens