Since the Habs won the Cup in 1993, these are the seasons, total amount of teams in the league each season, with the number on Canadian teams in the league as the third number:
1993-94 26 8
1994-95 26 8 - Nordiques moved to Denver after this season
1995-96 26 7 - Jets moved to Phoenix after this season
1996-97 26 6
1997-98 26 6
1998-99 27 6
1999-00 28 6
2000-01 30 6
2001-02 30 6
2002-03 30 6
2003-04 30 6
2004-05 lockout
2005-06 30 6
2006-07 30 6
2007-08 30 6
2008-09 30 6
2009-10 30 6
2010-11 30 6
2011-12 30 7 - Atlanta relocated to Winnipeg before this season started
2012-13 30 7
2013-14 30 7
2014-15 30 7
2015-16 30 7 - no Canadian teams even made the playoffs this year
2016-17 30 7
2017-18 31 7
2018-19 31 7
2019-20 31 7
2020-21 31 7
So there have been 789 total entrants since the Stanley Cup was last won by a Canadian franchise. 177 of those entrants were Canadian, and assuming that Tampa Bay close out the Habs in the next four games, an American franchise has won for twenty-eight straight seasons.
177/789 is 22.43%, meaning that all things being equal, you'd expect a Canadian team to have won the Cup 22.43% of the time, or about 6.28 Cups in total.
Including Seattle joining the league in a few weeks, and the Canadian teams staying at seven, seven years from now that would mean 226 Canadian entrants out of 1,013 entrants total since 1993, meaning that 7.8 Cups total should have been won by a Canadian entrant.
What this means is that the Canadian franchises could combine to win the next seven straight Stanley Cups in a row and they'd STILL be below average.
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