The biggest first-round upsets in Stanley Cup Playoff history

It feels strange calling this an "upset" because in 1971 the Canadiens were in the middle of a 15-year run that saw them win 10 Stanley Cups. But they had missed the playoffs entirely the year before and were playing a Bruins team that was 24 points better than them in the standings and had scored an almost unimaginable 399 goals during the regular season (in what was then a 78-game regular season). The Canadiens ended up winning a wild seven-game series that featured 54 total goals between the two teams on their way to yet another Stanley Cup. 

The 1981 Oilers had all of the key players that would go on to form their dynasty later in the decade (Wayne Gretzky, Jari Kurri, Mark Messier, and Glen Anderson were all 20 years old) but they were not yet at that championship level. This was also only the Oilers' second year in the NHL following the merger with the old WHA. The Canadiens, meanwhile, were still the dominant team in the NHL finished the regular season 29 points ahead of the Oilers in the standings. The Oilers not only won, they swept the best-of-five series in three games. They would lose in the second round to the New York Islanders who were just beginning their run of championships. 

It will never be confused with the Miracle on Ice, but the Herb Brooks coached Rangers pulled off a pretty stunning upset in the first round of the 1983 playoffs when they knocked off the heavily favored Philadelphia Flyers. The Flyers were 23 points better than the Rangers in the standings that year and won the regular season series by taking four of the seven games, but never got close in the playoffs. The Rangers won the series in three straight games, outscoring the Flyers by an 18-9 margin. 

There is no way to sugarcoat this, so let's just be honest. The 1985 Minnesota North Stars were awful. They finished the regular season with a 25-43-12 record and only made the playoffs because of the NHL's format at the time that took the top four teams in each division, regardless of record. There were 21 teams in the league, and 16 of them made the playoffs. The North Stars got in and actually swept a St. Louis Blues team that was 24 points better than them in the standings. 

Those pesky North Stars were at it again, taking advantage of a weak division to sneak into the playoffs with a terrible record. This time it was a 27-39-14 record that got them in the playoffs, and the postseason experience turned out to be even more improbable. The North Stars not only beat a Blackhawks team that was 38 points better than them in the standings, they used that to jumpstart what be a run all the way to the Stanley Cup Final where they would lose in six games to Mario Lemieux and the Pittsburgh Penguins. They are probably the worst team to ever reach the Stanley Cup Final. 

In their first two years of existence the Sharks were one of the worst expansion teams the NHL had ever seen, winning just 28 out of their first 164 games. They won 33 in year three and were good enough to snag a surprising playoff spot where they pulled off a stunning upset over a heavily favored Detroit Red Wings team that was just a couple of years away from taking over the NHL. The Sharks won the series in seven games with Jamie Baker scoring the game-winning goal late in the third period of the deciding game. 

The 1997 Oilers snapped a four-year postseason drought and completed a one-year turnaround that saw them go from being one of the absolute worst teams in the NHL to a playoff team. Their reward was a round one matchup against a Stars team that was one of the fiercest defensive teams in the league and on the verge of becoming a yearly championship contender. They would have to wait to reach that level because the Oilers stunned them in six games, winning three of them in overtime. 

The 1998 Devils were the No. 1 seed in the Eastern Conference and the second best team in the NHL. The 1998 Senators were a young team that was on the rise, but on paper not anywhere near the level of their first-round opponent. But that is why they actually play the games. The Senators stunned the Devils for their first postseason series win in franchise history. It was an incredibly close, low-scoring series with the Senators winning two games in overtime. The Senators may have lost in the next round but that season was the beginning of a 10-year run of sustained excellence that saw them reach the Conference Finals twice and the Stanley Cup Final once. 

For the second year in a row the Devils were upset in the first round in the 1 vs. 8 matchup. This time it came at the hands of a Penguins team that was literally fighting for its existence. The Penguins' financial situation was so bleak that had they lost in the first round it may have resulted in the relocation of the franchise. Jaromir Jagr, playing the series on one leg due to a significant groin injury, single handedly lifted the team to a Game 6 win to send the series back to New Jersey for a decisive Game 7 that the Penguins dominated. 

The 2001 Kings weren't necessarily a bad team, but the Red Wings were a legitimate Stanley Cup contender that was loaded with future Hall of Famers. When they took the first two games of the series by a combined score of 9-3 it just seemed like a formality that they were going to move on. Then the Kings ripped off four wins in a row, all by a single goal, to stun the Wings. Detroit would bounce back one year later by winning the Stanley Cup, but this was a team that seemed like it was capable of more than it accomplished. 

In 2003 the Colorado Avalanche were still at the height of their power, while the Wild were a third-year expansion franchise that was still making a name for itself. When the Avalanche raced out to a 3-1 series lead it seemed to just be a matter of when, and not if, they would close it out. The Wild had other ideas, winning three consecutive games (all by 3-2 scores), including Games 6 and 7 in overtime. The Wild did the same thing in the second round (overcoming another 3-1 series deficit) to reach the Western Conference Final. 

The 2006 Red Wings were 12 points better than any other team in the NHL that season and an incredible 29 points better than their first-round opponent. None of that mattered come playoff time as a scrappy Oilers team, led by Chris Pronger, Mike Peca, and a stunning goaltending performance from Dwayne Roloson, shocked the Red Wings in the first round on their way to a stunning run to the Stanley Cup Final. Had Roloson not been injured in that Stanley Cup Final series the Oilers probably would have won the whole thing. 

This is one of the teams that, unfortunately, made the Sharks organization synonymous with postseason underachieving. After winning the Presidents' Trophy with the league's best record, the Sharks opened the first round by losing the first two games of the playoffs on home ice and were never able to recover in the series, losing in six games to a team that finished 24 points behind them in the standings. The Sharks would end up reaching the Western Conference Final the next two years but were not able to break through to the Stanley Cup Final until 2016. They are still searching for their first championship. 

The 2010 Capitals were just plain fun to watch. They were one of the most dominant offensive teams of the modern era, were loaded with superstar talent, and had a power play that was as lethal as any unit you will ever see. Anyone that watched their series against the Montreal Canadiens knew they were the better team. But thanks to a superhuman effort from Jaroslav Halak the Canadiens were able to overcome a 3-1 series lead and stun the Presidents' Trophy winning Capitals. Then they did it again the next round, again led by Halak, against the defending Stanley Cup champion Pittsburgh Penguins. 

In hindsight this doesn't look like much of an upset because the Kings went on to win the Stanley Cup, and then did it again two years later. At the time, though, it looked to be a massive one. The Kings were the No. 8 seed and had to fight just to make the playoffs. The Canucks were the Presidents' Trophy winners with the league's best record and were two years removed from being in Game 7 of the Stanley Cup Final. The Kings wasted no time in jumping all over the Canucks, winning the first three games on their way to an easy and swift five-game series win.