Philadelphia Flyers  vs. Montréal Canadiens 
The Montréal Canadiens were not considered to be a team that was supposed to make the playoffs at the start of the season, but they surprisingly find themselves in their first playoff appearance since 2017. In the Eastern Conference Quarterfinals, they will face the Philadelphia Flyers. The most recent playoff appearance between the two teams was in 2010, in the Eastern Conference Finals, when Philadelphia defeated Montréal in five games. That series had the unusual distinction of having the two last seeded playoff teams facing off against each other in the Conference Finals, and thus far, it's the only time it has happened. Philadelphia won two of the three regular season games against Montréal in the regular season.
Prediction: Philadelphia in six games.
Tampa Bay Lightning  vs. Columbus Blue Jackets 
Towards the start of the regular season, many predicted the Columbus Blue Jackets would fall to last place in their division after losing three of their best players in the 2019 off-season. However, under coach John Torterella, the Blue Jackets had a surprisingly strong regular season, and managed to make the playoffs for the fourth straight season. Last year, they pulled off one of the most shocking upsets in NHL history when they swept the Tampa Bay Lightning in the opening round, which was amazing considering Tampa Bay had one of the best regular seasons in NHL history. The Blue Jackets will face the Lightning once again in the opening round for the rematch. Tampa Bay hopes to have learned from the mistakes that led to the epic collapse last year. During the regular season, Tampa Bay and Columbus met only once. That was on February 10, when Tampa Bay beat Columbus 2-1 in overtime.
Prediction: Tampa Bay in seven games.
Washington Capitals  vs. New York Islanders 
In 2018, the Washington Capitals won the Stanley Cup for the only time ever, and they were coached by Barry Trotz. Now, Trotz coaches the New York Islanders. Todd Reirden is now the head coach for the Capitals, and he hopes to help the Capitals win their second Stanley Cup. Last year, the Capitals were upset by the Carolina Hurricanes in seven games in the opening round. This is the eighth time the Islanders and Capitals meet in the playoffs; the Islanders have won five of the meetings so far. The Capitals won the most recent meeting in the first round of the 2015 playoffs. The teams met four times in the regular season. The Capitals won the first meeting on October 4 by a 2-1 score, the Islanders won 4-3 on December 31 on the second meeting, the Capitals won 6-4 on January 18, and the Islanders won 5-3 on February 10.
Prediction: Washington in five games.
Boston Bruins  vs. Carolina Hurricanes 
In 2019, Carolina ended a ten year drought of not appearing in the playoffs, and they made a very strong playoff run. They upset the defending Stanley Cup Champions, the Washington Capitals, in the opening round, and swept the New York Islanders in the second round. However, they disintegrated in the third round against Boston, and got swept in four straight. Carolina hopes to make up for the sweep. Boston ended up making their first Stanley Cup Finals appearance in six years, but lost to the St. Louis Blues in seven games. In the regular season, the two teams played against each other only once. That was on December 3, when Boston defeated Carolina 2-0. This marks the sixth time the Hurricanes and Bruins meet in the playoffs, although the first two times they met, Carolina was located in Hartford and known as the Hartford Whalers. The Bruins have won four of the five playoff meetings to date.
Prediction: Boston in six games.
Vegas Golden Knights  vs. Chicago Blackhawks 
The Chicago Blackhawks were the most dominant NHL franchise of the 2010s, winning three Stanley Cups (2010, 2013, and 2015). In 2017, they finished the regular season at the top of the Western Conference, but were surprisingly upset by the Nashville Predators in the first round. They shocked the hockey world by finishing last in the Central Division the following season. This season, they made the playoffs for the first time since 2017. Vegas shocked the hockey world in their inaugural season in 2017-18 by not only making the playoffs and having the best inaugural season in NHL history, but going all the way to the Stanley Cup Finals, when they fell to the Washington Capitals. Last year, they fell in the opening round. This meeting marks the first time that Vegas and Chicago will play each other in the playoffs. Of course, Chicago last made the playoffs in 2017, and Vegas entered the NHL in the following season, so this is also the first time that both teams appeared in the playoffs in the same year. Vegas won two of the three regular season meetings they had with Chicago. The Blackhawks are the first team to make the playoffs after finishing last in their division in the regular season since the 1980-81 Toronto Maple Leafs.
Prediction: Vegas in five games.
Colorado Avalanche  vs. Arizona Coyotes 
The Arizona Coyotes made it to the Stanley Cup Playoffs for the first time in eight seasons this year, ending the longest drought in franchise history without a playoff appearance. The Colorado Avalanche narrowly made the playoffs last season, but managed to upset the Calgary Flames in the opening round before losing in the second round. This season, the Avalanche were one of the best teams in the regular season, and have higher expectations for the postseason this time around, as opposed to having been an underdog a year ago. This marks the second time that the Coyotes and Avalanche meet in the playoffs. Their lone previous meeting was in 2000, when Colorado won in five games in the first round.
Prediction: Colorado in five games.
Dallas Stars  vs. Calgary Flames 
For the first time in almost 40 years, the Stars and Flames meet in the playoffs. The only other time the teams met was in 1981, when Dallas was still located in Minnesota and were known as the Minnesota North Stars; they defeated Calgary in six games in the third round of the playoffs. Calgary ended the 2018-19 regular season as the top team in the Western Conference, but were shocked in the opening round by the Colorado Avalanche four games to one. Dallas managed to defeat Nashville in the opening round in 2019, but fell to St. Louis in the second round (St. Louis eventually went on to win their first ever Stanley Cup). In the regular season, Calgary won two of the three meetings they had against Dallas.
Prediction: Calgary in seven games.
St. Louis Blues  vs. Vancouver Canucks 
The St. Louis Blues won their first ever Stanley Cup in 2019, and they look to win their second straight in 2020. In the Western Conference Quarterfinals, they face the Vancouver Canucks, who have made the playoffs for the first time in five years. St. Louis and Vancouver have met three times in the playoffs so far, and Vancouver has won every single won of them thus far. The most recent meeting between the two teams was in 2009, when Vancouver swept St. Louis in four straight games. With St. Louis having won the Stanley Cup last season and having more playoff experience, St. Louis hopes the fourth time will be the charm. Vancouver won two of the three regular season meetings they had with St. Louis.
Prediction: St. Louis in six games.