Best NHL Stanley Cup Playoffs Teams of 21st Century

Winning the Stanley Cup out of the parity of the NHL is the ultimate challenge. Just ask the four 2019 division winners who each lost in the first round of the Stanley Cup Playoffs, the first time that has happened in a major professional sport in North America.

Only four teams have hoisted the iconic trophy multiple times in the 21st century, not counting the New Jersey Devils, who won in 2003 after winning at the turn of the milennium in 2000.

The Boston Bruins (who won in 2011 and are now knotted with the Columbus Blue Jackets 1-1 in the conference semifinals), Carolina Hurricanes (the 2006 champions who lead the New York Islanders, 2-0) and Colorado Avalanche (winners in 2001, tied 1-1 with the San Jose Sharks) can join that list in 2019. 

Here's a look at the multiple-time Cup winners since 2000:

Pittsburgh Penguins: The Sidney Crosby-led Penguins have won 3 Stanley Cups, including back-to-back wins in 2016 and 2017, the first team to accomplish that feat in 19 years and the first since the salary cap was introduced. 

Chicago Blackhawks: The Chicago Blackhawks took home 3 Stanley Cups in a six-season span: 2010, 2013 and 2015. From 2009-2015, the 'Hawks had a points percentage greater than .600 in every season but one, behind a core of Patrick Kane, Jonathan Toews and Marian Hossa.

Los Angeles Kings: The Kings won two Stanley Cups in three years. Their 2012 run was a Cinderella story: The eighth-seeded Kings became the first team in history to eliminate the No. 1 seed and No. 2 seed on their way to the finals. The 2014 run was also historic: They became the first team to win three Game 7s en route to the Stanley Cup.

Detroit Red Wings: From 2001-2011, the Red Wings won nine division titles, three conference championships and two Stanley Cups -- in 2002 and 2008, when they knocked off the Penguins in 6.

By Ryan Kroll