2020 Stanley Cup Playoff Predictions

Updated: Aug 7


Lord Stanley's Cup... Some would call it the most coveted and mysterious trophy in all of sports. Hockey players from all over the world have childhood dreams of one day raising Stanley over their head in victory, in the most competitive and famous professional hockey league in the world. We hockey fans know that nothing compares to the Stanley Cup Playoffs. It seems that every year we are treated to something new, something historical, something that ends in triumph and glory for some, but heartbreak and tears for most.


Whether it be the 1924 Montreal Canadiens leaving the Cup on the side of the road after changing a flat tire, or the 1994 New York Rangers feeding Kentucky Derby winner Go for Gin from the top of the Cup at Belmont Park, every year the Cup's story gets a little more weird.


This year's chaos and drama will feature expanded playoffs, hub cities, no fans, and hopefully a season that can finally conclude with the Stanley Cup being won for the first time ever during a global health pandemic. Let's get into the predictions, round by round, of who I think is going big, and who is going home.



The Play-In Round:


Remember! The Play-In round is a best of five series. It is not a traditional best of seven series like the later rounds will be.


Note: This is also assuming that the top four seeds in each conference keep their seeding.


Toronto Maple Leafs (8) vs. Columbus Blue Jackets (9)


The Columbus Blue Jackets are coming off of delivering one of the biggest upsets in sports history. In 2019, the Wild Card Blue Jackets handed the first seed and Presidents Trophy winner Tampa Bay Lightning a first round sweep. Why is this that big of a deal you ask? First seeds get upset in sports quite frequently? While you are correct, this was especially different. Tampa Bay was coming off of a season where they racked up 128 points during the regular season. Making them the fourth most winningest team in NHL history right behind the 1977-78 Montreal Canadiens who racked up 129 points.


But with that being said, Columbus did lose their best player in Artemi Panarin to free agency when he signed with the New York Rangers, and one of the top goaltenders in the league when Sergei Bobrovsky signed with the Florida Panthers. I think at the end of the day, Toronto's offense overwhelms Columbus fast, and while the Blue Jackets might squeak out a game or two, I give this series to Toronto.


Winner: Leafs in 4.




Pittsburgh Penguins (5) vs. Montreal Canadiens (12)


One key word comes to mind when this series is brought up - EXPERIENCE.


Sidney Crosby, Evgeni Malkin and the Pittsburgh Penguins have won 2 Stanley Cups in the last 5 years, and 3 in the last eleven. The relatively young Montreal Canadiens struggled all year in the overwhelmingly stacked Eastern Conference, and while I believe the Canadiens have a bright future ahead of them and will be serious Cup contenders within the next five years with goaltender Carey Price at the helm, this year just isn't their year. I do believe the experience of Carey Price can help Montreal manage to get at least one win though.


Winner: Penguins in 4.



Carolina Hurricanes (6) vs. New York Rangers (11)


Lets get it out of the way early, love it or hate it, before the season was paused, the Rangers were red-hot. Before the NHL paused play due to COVID-19, the Rangers were riding a 14-7-1 record, and were cruising into a Wild Card spot. The Carolina Hurricanes knew this, and that is why they were one of two teams to vote against the expanded playoffs when the league first put it to vote.


The Rangers have quite the young core. Igor Shesterkin with his nasty .932 save percentage and 10-2 record since being called up, and a defensive stud in Adam Fox are who stick out right away. If it weren't for Quinn Hughes (VAN) Cale Makar (COL) and Dominik Kubalík (CHI) tearing it up in the western conference, Adam Fox would certainly be a Calder Memorial Trophy candidate. But sadly for Rangers fans, he just missed the cut, and even more sad for Rangers fans, this is probably Henrik Lundqvist's last ride in a Rangers sweater. I can't see head coach David Quinn starting Lundqvist in goal over Shesterkin or Alexandar Georgiev, especially since the games will not be played in front of the MSG crowd that has passionately adored him over the last 15 years.


Carolina has the opposite problem that the Rangers have. They are desperate for goal-tending. The Hurricanes do however have all-star center Sebastian Aho leading the offense, and are getting Dougie Hamilton back from injury heading into the series. Hamilton was a Norris Trophy candidate before falling victim to injury in December. Carolina's only hope of winning this series is if their defense can shut down the Rangers red-hot offense, and give their scarce goal-tending talent a fighting chance - Which is very do-able since the Hurricane's GAGP (Goals Against Per Game) ranks 12th in the league.


I see this being a very close series but in the end...


Winner: Rangers in 5



New York Islanders (7) vs. Florida Panthers (10)


Florida will be a tough match-up for the Islanders. The Panthers are the superior offensive team in this match-up, but the Islanders have the upper hand in the defensive category. Not only that, but the Islanders have owned the Panthers in the 2019-20 season. New York swept Florida in the season series, and just four years ago in the 2016 playoffs the Islanders knocked off the Panthers. Sergei Bobrovsky will be a tough nut to crack for the Islanders offense, which struggled in the latter half of the season, dropping 8 or their last 10 games, and not winning a single game since the big Jean-Gabriel Pageau trade + extension... But the Islanders have had time to recover, and coach Barry Trotz has had more than enough time to revise his play book that was failing to work before the pause.


In a very, very close series between two evenly matched teams...


Winner: Islanders in 5



Edmonton Oilers (5) vs. Chicago Blackhawks (12)


The Edmonton Oilers have the luxury of employing the best hockey player in the world currently - Connor McDavid. But don't get it twisted, outside of McDavid, the Oilers are not to be messed with. Connor McDavid has the perfect co-star in Leon Draisaitl who is one of three Hart Memorial Trophy candidates. This (to me) is enough to put the Oilers over the Blackhawks in a short series. But much like I said about the Penguins, the Blackhawks have the experience needed to win. Chicago is the NHL's last great dynasty. Winning Stanley Cup's in 2010, 2013, and 2015. Not to mention, Patrick Kane still has what it takes to turn it on and put his team on his back.


Winner: Oilers in 4



Nashville Predators (6) vs. Arizona Coyotes (11)


Arizona have an impressive team, even for an eleven seed. But if this article has taught you anything so far, its that it doesn't matter what seed your team is sitting in, the NHL does not have a shortage of spectacular talent. Taylor Hall, Phil Kessel, Clayton Keller, and Conor Garland are all guys who can step up and help carry this Coyotes team to a series win.


The Predators have been a shaky team since their 2017 Stanley Cup appearance. But Nashville still has Pekka Rinne in goal, and they still have guys like Roman Josi and Filip Forsberg.


Nashville is plenty capable of winning this series.


Winner: Coyotes in 5.



Vancouver Canucks (7) vs. Minnesota Wild (10)


I am going to come right out and say it, I have a soft spot for the Wild. How could you not love the state of hockey? But the sad reality is that the Wild have been in bad condition for years now. The top hockey market in the United States deserves better than what they have. The Wild are old and tired.


On the complete opposite side of this match-up, the Canucks are young, fast, and hungry. The Canucks have no shortage of young talent. Jacob Markström has had a sneaky good year, who would have expected that? And they have young rookie phenom Quinn Hughes.


Winner: Canucks in 3.



Calgary Flames (8) vs. Winnipeg Jets (9)


Winnipeg's defense was depleted due to free agency during the off-season. Who expected the Jets to be where they are at now? Not me, but I'll bet Connor Hellebuyck did. Hellebuyck DOMINATED this season. And it was exactly what Patrik Laine, Blake Wheeler and co. needed in order to contend this season.


Calgary has a solid 1-2 punch of their own in the scrappy, never back down Matthew Tkachuk (son of United States Hockey Hall of Famer Keith Tkachuk, and brother of Ottawa Senators Brady Tkachuk) and Johnny Gaudreau, which gives Calgary a solid chance at taking this series.


Winner: Jets in 5



The First Round:


Boston Bruins (1) vs. Toronto Maple Leafs (8)


This will be the third consecutive year that the Toronto Maple Leafs and Boston Bruins have met each other in the first round. In the last three years, Toronto has failed to take down Boston. The Bruins seem to be the thorn in the side of the Leafs. Toronto won't back down without a fight, but I can very easily see Boston overwhelming Toronto in the end. Brad Marchand and co. will lick the competition goodbye.


Winner: Bruins in 6



Tampa Bay Lightning (2) vs. New York Islanders (7)


Tampa has something to prove this year. All you have to do is go back to what I said in regards to their embarrassing playoff exit last year to know that the Lightning are on a war path to prove the hockey world wrong and that they aren't a mistake. They're here as a top team and they're here to dominate.


The Islanders have however been good against Tampa this year. They went 2-1-0 against the Lightning this year, and even though it is a small sample size, the Islanders have bragging rights over the season series.


I have a very hard time believing that the Lightning let themselves go out in the first round again two years in a row.


Winner: Lightning in 6



Washington Capitals (3) vs. New York Rangers (11)


The Rangers and the Capitals meet in the playoffs once again. These two teams have been the fiercest of playoff rivals over the last 5 years, with the Capitals getting the last laugh by taking home the Stanley Cup in 2018, something the Rangers failed to do in 2014 when they were beaten in the Cup Finals in 5 by the Los Angeles Kings.


New York will give Washington a run for their money. Artemi Panarin and his co-star Mika Zibanejad are poised to take over the NHL in the next few years, and are not to be slept on. Real hockey fans recognize those names. New York also holds the season series win with a 2-1-0 record. And who knows, maybe the young, impressionable Russian Igor Shesterkin can gain the respect of his older, legendary countryman in Alexander Ovechkin with a few mind-blowing saves.


Winner: Capitals in 6



Philadelphia Flyers (4) vs. Pittsburgh Penguins (5)


This. This is the series that you want to see out of the east. There is so much bad-blood between these fierce interstate rivals. You cannot talk about the best rivalries in sports without mentioning Flyers vs. Penguins. From playoff fights, to trash talk in locker rooms, to guys literally (and admittedly) trying to end each others careers with dirty hits, this is everything you want to see in a playoff hockey series.


The Flyers look legit this year. Ex-Rangers head coach Alain Vigneault has come into Philadelphia and has done a tremendous job with this team. The Flyers are solid all around the board. Offense, defense and goal-tending has been phenomenal for Philadelphia this year. The Flyers are just plain and simple, a better team all around than the Penguins are. Do not expect the Penguins to just lay down and let Philly have it though, because they will not give up that easily.


Winner: Flyers in 5



St. Louis Blues (1) vs. Winnipeg Jets (9)


The defending Stanley Cup champions are back, and ready to take the Cup back to Missouri. St. Louis' regular season performance has shown no sign of slowing down since defeating the Boston Bruins in 7 games to clinch their first Stanley Cup title in franchise history. In less than two seasons Jordan Binnington has solidified himself as a top goalie in the NHL for a long time to come. Getting back a healthy Vladimir Tarasenko will certainly help boost the Blues' odds to repeat.


The Jets will make this an interesting series. They are a hard nosed, blue collar, no nonsense team and they will do their very best to upset St. Louis.


Winner: Blues in 5



Colorado Avalanche (2) vs. Vancouver Canucks (7)


In the battle of offense, Colorado vs Vancouver will have all the fireworks. I give a slight edge to Colorado because of the fact that Vancouver is a very young team.


This could be a great series for the casual fan because of the high volume of offense this series should provide for us. I predict that the Avalanche will be the better of the two teams however, even with Markström on his A game in goal. Vancouver's defense will ultimately end up failing to keep up with the speedy talented Avalanche offense.


This series will also feature two of the three Calder Memorial Trophy candidates, which means that if you want to see the future of the NHL in action, tune into this series.


Winner: Avalanche in 5



Vegas Golden Knights (3) vs. Arizona Coyotes (11)


Hot take incoming: The Knights are the best team coming out of the west this year despite being the three seed.


While the Coyotes will surprise everyone by getting this far, I don't think this series will feature too much competition. Vegas will cruise. There isn't much left to say about it until the next round.


Winner: Golden Knights in 4.



Dallas Stars (4) vs. Edmonton Oilers (5)


This will probably prove to be the closest series in the west so far. You just cannot say enough about Connor McDavid. He's the Mike Trout of hockey, he's the Patrick Mahomes of hockey. He's just that good. Leon Draisaitl and Connor McDavid will be a threat to anyone they face.


Dallas is a great team this year. Good enough to land them the fourth seed over some really good western conference teams. This series will come down to what each team can do in the offensive zone, and you have to give the edge to Edmonton in that category.


Winner: Oilers in 7



Conference Semifinals:


Boston Bruins (1) vs. Philadelphia Flyers (4)


Boston is once again close to glory. Brad Marchand can taste it every time he sticks out his tongue. (I know that's the second Marchand lick joke I've made but I still can't believe he was licking people on ice)


Philadelphia is trying to win their first Cup since 1975, and trying to make their first appearance since 2010. The Flyers are trying to erase a 45 year drought.


Both teams are just 12 wins away from getting their names enshrined on Lord Stanley's Cup. Who will prevail? If the Flyers want it, they have to get to Tuukka Raask fast. The Bruins biggest strength is their defense and their goalie.


But the Flyers are trying to prove that the Bruins don't belong here. And that last year's Cup appearance for Boston was a fluke.


Winner: Bruins in 7



Tampa Bay Lightning (2) vs. Washington Capitals (3)


Reigning Hart Memorial Trophy winner Nikita Kucherov and his Tampa Bay Lightning still haven't redeemed themselves from last years sweep at the hands of the Blue Jackets. They still have to silence the doubters and haters. The hockey world is still laughing at them and they know it.


Alexander Ovechkin, T.J. Oshie and Braden Holtby are trying to hoist the Cup one more time. Washington is looking to join the ranks of teams like Pittsburgh, Los Angeles and Chicago as the fourth team to win multiple Cups in the last 11 years years. They refuse to be one-and-done.


Tampa Bay is 0-2-1 against Washington this season, but as hockey fans know, once the playoffs start, anything can happen.


Winner: Lightning in 7



St. Louis Blues (1) vs. Edmonton Oilers (5)


I've been hyping up Edmonton a lot until now. I've been fan-boying over Connor McDavid, I know. But this is where the Oilers face their biggest challenge. I hate to say it, but it won't matter if Connor McDavid and Leon Draisaitl play the best series of their careers thus far. This seems to be the end of the line for Edmonton.


Jordan Binnington will likely spend a majority of this series on his head, but Alex Pietrangelo and Jay Bouwmeester will do their best to keep the firey Edmonton offense at bay, while Vladimir Tarasenko and Ryan O'Reilly lead the St. Louis offense down the ice to take care of things on the other side.


Winner: Blues in 5



Colorado Avalanche (2) vs. Vegas Golden Knights (3)


Like I said earlier, Vegas is my favorite team coming out of the west. But you obviously can't discredit the two seed Avalanche who have a very good chance of taking this series for themselves. That is why I am very much looking forward to this potential match-up.


The Edge goes to Vegas because of their goal-tending situation. They have Marc-André Fleury and recent acquisition and goalie sensation in his own right, Robin Lehner. Even if Vegas' head coach Peter DeBoer opts to alternate goal-tenders night after night (I'm not sure why he would but lets just say,) Vegas will always have the better goalie.


Colorado's goal-tender Philipp Grubauer is a solid goalie, but Colorado isn't rich with goal-tending like Vegas is. If Grubauer isn't on his A game, Vegas will take advantage of that. And it's not like Colorado has the luxury of removing Grubauer for someone like Fleury or Lehner like Vegas does.


Winner: Golden Knights in 6.




Conference Finals:


Boston Bruins (1) vs. Tampa Bay Lightning (2)


Here it is, two teams who have been trying for years to hoist another Stanley Cup. The Bruins last Cup win came in 2011, while Tampa Bay's last Cup win came in 2004. Both teams are hungry and coming off heartbreaking 2019 campaigns. The Bruins being defeated in 7 games against St. Louis in the Cup Finals, and Tampa Bay suffering a sweep in the first round last year at the hands of the Columbus Blue Jackets.


At this point, the Tampa Bay doubters are quiet. Boston haters are on the edge of their seat. The city of Montreal is at an extremely high stress level due to the thought that their biggest rivals - the Boston Bruins - might make two consecutive Cup appearances.


And this time they might be for real.


Winner: Bruins in 6



St. Louis Blues (1) vs. Vegas Golden Knights (3)


The Blues just watched Boston defeat Tampa Bay in 6 games. St. Louis knows they can beat Boston when it matters, because they've proven they can before.


Vegas wants to get back to the Cup Finals. They were beaten by the Washington Capitals in 2018 and they immediately caught the attention of the entire nation by being an expansion team in their first year to reach the Cup Finals. This time they want to show that they can finish the job. The Vegas front office knows hockey, they know what they're doing with this team. There's no other way you can explain them being this good with only 3 years in the league and being a dominant force in the west for 3 years.


Winner: Vegas in 7



The Stanley Cup Finals:


Boston Bruins (1) vs. Vegas Golden Knights (3)


This. Is. It. East vs. West. Winner takes all. The hardest trophy in all of sports to win, and its down to two teams. For the 27th consecutive year, a Canadian team will not be hoisting the Stanley Cup. Two teams who suffered defeat in the last 3 years are back. One of them will face heartbreak one more time. For the other, the waiting will finally be over. They will be enshrined into hockey history.


Once again, Vegas' biggest strength will be their goal-tending situation. But make no mistake, the goalie at the other end of the ice is not to be taken lightly.


David Pastrnak, Charlie McAvoy, Zdeno Chára and Brad Marchand lead the way for the Bruins.


William Karlsson, Max Pacioretty, Mark Stone, and Jonathan Marchessault oppose them from across the red line.


Both parties have Stanley Cup experience, both parties know what its like to lose the ultimate prize. Players on both sides also know what its like to sip champagne out of the most coveted trophy in sports.


In a very evenly matched series between two very similar teams, only one can win.


2020 Stanley Cup Champions: Boston Bruins in 6.



Here is the recap of my 2020 Stanley Cup predictions












Please remember, these are just my predictions. As you probably know it is almost impossible to have near perfect predictions in sports, even for the most seasoned industry professionals. If you would like to talk hockey and give me your input on what you would like to see, comment, like and follow the blog! I'm always open to a civil sports chat.


Thank you so much for reading. Be safe out there.


- Chris

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