Top 5 most shocking first-round Stanley Cup Playoff upsets in NHL history

The Canadiens went on to beat the Pittsburgh Penguins in the second round before being eliminated in the Eastern final against the Philadelphia Flyers. Still, Montreal fans will forever remember the way the Habs cracked down on defense to upset the Capitals.

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4. Edmonton Oilers defeat Montreal Canadiens (1981)

The Canadiens were the Western Conference’s best regular-season team in the 1980-81 campaign, and that sent them into a showdown against the Oilers, who had 29 fewer points than Montreal.

However, in the best-of-five first-round series, the upstart Oilers swept the Habs, outscoring them 15-6. Edmonton superstar Wayne Gretzky had three goals and 11 points against Montreal – and although the Oilers lost to their arch-rival, the New York Islanders, in the second round, this was the farthest a Gretzky-led Edmonton team made it out of the first round, laying the foundation for their first Cup in 1983-84.

The Canadiens came closest to winning in 1981, tying Game 2 1-1. But Gretzky and fellow star Jari Kurri combined for four points in the Oilers’ final two Game 2 goals, and Game 3 was a 6-2 rout. It wasn’t a changing-of-the-guard moment in hockey history, as Montreal won another Cup in 1985-86. But it was a harbinger of the Oilers’ dominance to come.

3. Montreal Canadiens defeat Boston Bruins (1971)

The Bruins entered the 1971 post-season with the league’s best regular-season record, and they had 24 more points than Montreal did. But the Canadiens’ first-round series against Boston was all about the heroics of Habs rookie goaltender Ken Dryden. The Hockey-Hall-of-Fame netminder dazzled in his NHL playoff debut, leading the Canadiens to their 16th Cup while winning the Conn Smythe Trophy as playoff MVP.

Along with dominant star forward Frank Mahovlich, Dryden powered Montreal past Boston in seven games in their first-round showdown. The Canadiens would also beat the Minnesota North Stars and the Chicago Blackhawks in the 1971 playoffs.

Dryden went on to win another five Cups for a total of six in his eight-year NHL career. But the first Cup was probably the sweetest, as it set in motion a stretch of supremacy rarely seen in hockey history. It all started with the elimination of the heavily-favored Bruins.

Columbus Blue Jackets IMAGN 042226

Imagn Images

2. Columbus Blue Jackets defeat Tampa Bay Lightning (2019)

There hasn’t been a wealth of great playoff moments for the Blue Jackets, but the 2018-19 playoffs saw Columbus take on the Presidents’ Trophy-winning Tampa Bay Lightning in Round 1. And shockingly, not only did the Jackets upset the Bolts – they swept them.

The series lasted only six days, with Columbus dominating Tampa Bay from early in the second period of Game 1 through to Game 4’s 7-3 shellacking that sent the Lightning home for the summer. The Blue Jackets never trailed for a single minute in their final three games of the series, outscoring Tampa 15-5 in those final three games.

The Lightning would ultimately shake off the defeat by winning two Cups in the next two seasons, but it changed the philosophies and mindset of coach Jon Cooper and the Lightning organization. The Blue Jackets, however, lost in the second round to the Bruins in 2019, and they’ve only won one playoff series since then.

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1. Los Angeles Kings defeat Edmonton Oilers (1982)

The 1981-82 first-round series between the Kings and Oilers included a game famously nicknamed ‘The Miracle On Manchester’ – but that’s just one part of this unforgettable, best-of-five series. That’s in part because few gave Los Angeles much chance of beating Gretzky’s powerhouse Oilers, who were 48 points better than the Kings

But the playoffs would be a different story.

In Game 1, the Kings shocked Edmonton, beating them 10-8. The Oilers won Game 2 on a Gretzky overtime goal. Then came Game 3 – ‘The Miracle On Manchester’: the Oilers built a commanding 5-0 lead, but the Kings scored the next six goals – including the overtime winner – to give them a 2-1 series lead.

The Oilers still had fight in them, winning Game 4 to send the series to a fifth game. But the Kings completed the upset by steamrolling Edmonton 7-4. Gretzky had seven assists and 12 points in the series, but L.A. wasn’t to be denied.

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