Top 10 Biggest Upsets in Stanley Cup Playoff History

How did this happen? What went wrong? These are the questions typically asked when a powerhouse is inexplicably knocked off by a scrappy underdog in the Stanley Cup Playoffs. What makes upsets all the more shocking in hockey, compared to say football or soccer, is that in those sports, it's just one game. Flukes can happen, a team can have a bad day. In the Stanley Cup Playoffs, the underdog has to beat the favourite four times in seven games or less to advance. It makes it all the more shocking when that feat is accomplished. Don't follow those regular season stats too religiously, because anything can happen in the playoffs. Here are the 10 most shocking upsets in the history of the Stanley Cup Playoffs.


10 Anaheim Mighty Ducks over Detroit Red Wings (2003)

The Mighty Ducks of Anaheim looked like a complete mismatch going up against the defending champion Detroit Red Wings in 2003.

Detroit's roster was filled with future Hall of Famers, Steve Yzerman, Brendan Shanahan, Nicklas Lidstrom, and Chris Chelios. They also had Sergei Federov, Brett Hull, Luc Robitaille, Matthew Schneider and a couple of young studs in Henrik Zetterberg and Pavel Datsyuk. The Red Wings were the second seed in the Western Conference, finishing with 110 points, just one behind Dallas for first. Though the Stars finished first, many expected the Red Wings to make a run for a second straight Stanley Cup.

They ran into a Ducks team with Paul Kariya leading the way, along with Adam Oates, Petr Sykora and Steve Rucchin. They had some hard-working players in Steve Thomas, Rob Niedermyer and Sandis Ozolinsh. Overall, a young team with solid veteran leadership.

The great equalizer for the underdog Mighty Ducks was a hot goaltender in Jean Sebastien Giguere. Giguere stopped 64 shots in a Game 1 win and allowed just six goals in the entire series. A short series.

Not only did Anaheim knock off the Red Wings, they swept them. All four wins were decided by one goal, but Mike Babcock's Ducks shocked the hockey world. When Steve Rucchin scored the overtime series winner in Game 4, everyone was dumbfounded. The Ducks rode a magic carpet to the Stanley Cup Final. After their sweep of the Red Wings, nothing they did surprised anyone.

9 Chicago Black Hawks over Toronto Maple Leafs (1938)


Teams with sub .500 records could only win the Grey Cup, right? Well, there was a time when a sub .500 team won the Stanley Cup.

The 1937-38 Black Hawks (it was two words back then), made the playoffs despite finishing with an overall record of 14-25-9 for 37 points. The NHL was an eight-team league at the time, with six teams making the playoffs. Luckily for Chicago, Detroit was worse.

The Black Hawks took down the Canadiens and the New York Americans to reach the final, but surely the top seeded Maple Leafs would finish them off, right? Nope. Chicago took the Stanley Cup, beating Toronto three games to one, pulling a feat we'll never see again. Finishing a regular season below .500 and making the playoffs is nearly impossible as it is in a 30-team league, much less winning the cup.

8 Toronto Maple Leafs over Montreal Canadiens (1945)

There was a time before us, you know.

The 1944-45 Montreal Canadiens were the defending Stanley Cup champions and set the world on fire in 1945. In a 50-game season, they finished with a record of 38-8-4, a winning percentage of .800. They finished with a goal differential of +107. Maurice Richard scored 50 goals in 50 games as part of the "Punch Line" with Toe Blake and Elmer Lach. The line finished first, second and third in league scoring.

The Maple Leafs came into the semifinals seemingly with no chance, sporting a 24-22-4 record, but goalie Frank McCool was up to the task. They took the first two games in Montreal then dropped Game 3 at home. They took the next game 4-3 in overtime, heading to Montreal with a 3-1 series lead. The Canadiens' attack finally exploded, winning the fifth game 10-3.

However, Toronto would complete the shocking upset back at Maple Leaf Gardens in Game 6, as McCool led them to a 3-2 win.

Toronto went on to win the Stanley Cup in seven games over Detroit. This was probably the best Canadiens team to not win the Stanley Cup.

7 San Jose Sharks over Detroit Red Wings (1994)


The Detroit Red Wings went through many playoff failures before ending a 42-year cup drought in 1997. One such failure that stands out is their loss to the three-year-old franchise that was the San Jose Sharks in 1994.

After an 11-win season in 1992-93, the Sharks qualified for the playoffs in 1994. Their reward? An opening-round series with the NHL's highest scoring team, the Detroit Red Wings. The Sharks had Sandis Ozolinsh, Sergei Makarov, Igor Larionov, Todd Elik and Arturs Irbe. Good players, but no match for Yzerman, Federov, Ray Sheppard, Paul Coffey and Keith Primeau, right?

The gap in the standings was only 18 points, but no one gave the pesky Sharks a chance. The Wings scored their share of goals in this seven-game series, but the Sharks matched the Wings punch for punch.

In Game 7, Jamie Baker scored a go-ahead goal at 13:25 of the third period, when Chris Osgood was caught out of position. The Sharks held on for a 3-2 win and their first series victory in franchise history.

6 San Jose Sharks over St. Louis Blues (2000)

The St. Louis Blues enjoyed one of their best seasons in franchise history back in 1999-2000, winning the Presidents Trophy with 113 points. Many thought this would finally be the year they would win it all.

They drew the lowly Sharks in Round 1, who squeaked into the playoffs with 87 points.

However, after four games, San Jose unbelievably had the powerful Blues on the ropes with a 3-1 series lead. Steve Sheilds was clearly the superior goaltender in the series, as Roman Turek let in several shaky goals.

The Blues' offense came to life, winning 5-3 and 6-2 to force a Game 7 back in St. Louis. So the sleeping giant was awoken and now the Sharks would go away, right?

With time winding down in the first period, Owen Nolan slapped a shot from centre ice that got past Turek, giving the Sharks a 2-0 lead. It proved to be the series winner, as San Jose won the game 3-1. Blues fans must still have nightmares about that long shot.

5 Montreal Canadiens over Washington Capitals (2010)


Carey Price is now the cornerstone of the Habs franchise, but fans in Montreal still haven't forgotten the performance of Jaroslav Halak in the 2010 playoffs.

The Canadiens entered as the eighth seed against the Washington Capitals, winners of the Presidents Trophy with 121 points, 33 more than the Habs' 88. They set franchise records and many thought it was finally the year Alex Ovechkin would lead the Caps to the promise land.

Then they hit a Slovak wall in Halak.

They certainly looked to be on their way, opening a 3-1 series lead heading back to Washington for Game 5. Montreal was dead in the water and the Capitals' offense was everything as advertised, winning games by scores of 6-5, 5-1 and 6-3. No eighth seed had ever overcome a 3-1 deficit against a no.1 seed.

Halak proceeded to stop 37 of 38 shots in Game 5 for a 2-1 win. He then turned in perhaps the greatest single-game goaltending performance in Habs' franchise history, stopping 53 of 54 shots in a 4-1 win in Game 6. The upset was complete in Game 7 when Halak stopped 41 shots in a 2-1 win.

Halak carried the Canadiens to the Eastern Conference Finals before they were ousted by the Flyers.

4 New York Islanders over Pittsburgh Penguins (1993)

The Pittsburgh Penguins of the 1990s were filled with talent but fell short of becoming a dynasty.

After winning back-to-back cups in 1991 and 1992, they seemed destined for a three-peat in 1993. Mario Lemieux had successfully returned from Hodgkins disease to lead the league in scoring, Jaromir Jagr was better than ever, Ron Francis was in his prime, everything was clicking. They stormed into the playoffs on a 17-game winning streak.

The Islanders were missing Pierre Turgeon and just had a gruelling series with the Washington Capitals. The Penguins waltzed over New Jersey in five games.

The Islanders answered the bell, and forced a seventh game in Pittsburgh. David Volek snapped home a one-timer in overtime past Tom Barrasso to win the game and series 4-3 and put an end to Pittsburgh's dynasty hopes.

Sadly for the Islanders, they haven't won a playoff series since.


3 Edmonton Oilers over Detroit Red Wings (2006)


The Oilers came into the 2006 playoffs as the eighth seed, drawing the Presidents Trophy winners, the Detroit Red Wings in the opening round. The Wings finished the season with 124 points, 29 more than the Oilers' 95.

Coming off the 2004-05 NHL lockout, Detroit showed they had not lost their way and their veteran leadership was as strong as ever, with Yzerman, Shanahan, Lidstrom, Chelios and Robert Lang leading the way.

The Oilers had Ryan Smyth, Chris Pronger, Ales Hemsky and Dwayne Roloson in net. A good team, but one that would clearly be overpowered. Or so everyone thought.

The Oilers split the first two games at the Joe, with Roloson stopping 87 of 92 shots in the two games. They split the two games in Edmonton as well, before the Oilers took the pivotal Game 5 in Detroit, hanging on for a 3-2 win.

In an electric atmosphere at Rexall Place, the Oilers came back from a two-goal deficit in Game 6. With the game tied 3-3, Ales Hemsky took a beautiful feed from Sergei Samsonov and beat Manny Legace with just 1:06 left. The Oilers took the series and their Cinderella run took them to the seventh game of the Stanley Cup Final.

2 Montreal Canadiens over Boston Bruins (1971)

All hockey experts could ask themselves in 1971 was, 'who is this kid in net stoning the Bruins?' The answer was a rookie named Ken Dryden.

The Boston Bruins were the defending Stanley Cup champions. They finished the 1970-71 season with 121 points and 57 wins. The Montreal Canadiens had a respectable 97 points, but were entering the playoffs riding a rookie goaltender with just six NHL starts under his belt.

In his first playoff series, he'd be facing Phil Esposito, riding a 76-goal, 152-point season. Bobby Orr posted 139 points and the Bruins' onslaught was supposed to chase Dryden out of the Boston Garden.

The series is remembered for the Habs' comeback in Game 2. Down 5-1, they posted six straight goals to win 7-5.

The Canadiens eventually forced a seventh game, and stunned the Boston crowd with a 4-2 victory in Game 7.

The series win led the Canadiens to a Stanley Cup in 1971 and propelled their 70s dynasty as they won six cups over the course of the decade.

1 Los Angeles Kings over Edmonton Oilers (1982)


The Edmonton Oilers were young, confident and set to go on a Stanley Cup run. They were eager to dethrone the New York Islanders and all they had was this tiny speed bump in the Los Angles Kings to get through first.

The Oilers finished the 1981-82 season with 111 points and a record of 48-17-15. The matchup with the Kings was laughable, as L.A was 24-41-15 with 63 points. A 48-point difference!

Edmonton was full of young stars in Wayne Gretzky, Mark Messier, Jari Kurri, Glen Anderson, Paul Coffey and Grant Fuhr. Gretzky scored 92 goals, and racked up 117 assists for 212 points!

The Kings were carried by Marcel Dionne, who just had a 50-goal season.

The Kings splitting the first two games in Edmonton was shocking enough, then it happened; the Miracle on Manchester.

The Oilers opened up a 5-0 lead in Game 3, seemingly having solved the Kings and appeared set to roll on to the next round.

The Kings then scored five goals in the third period, tying the game with five seconds left Steve Bozek slipped a puck through Fuhr to tie the game at 5. Daryl Evans slapped a puck over Fuhr's arm early in overtime to complete the historic comeback.

The Oilers forced a deciding game back in Edmonton, but they were clearly rattled. The Kings completed the upset with a 7-4 win in Game 5. The Oilers would go on to win four cups in the 80s while the Kings' fortunes didn't turn until they acquired Gretzky in the summer of 1988.

It's unlikely in today's NHL we'd ever see a 48-point differential in a playoff matchup, and as a result, this upset will never be matched.

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