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Most memorable Stanley Cup wins in history

The Stanley Cup is one of the most exciting tournaments in professional sport. Every year, the best teams compete to get their hands on the famous trophy. And there have been plenty of shocks, thrilling games, and longshot Stanley Cup winners throughout the years. Here are some of the most memorable.

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Most memorable Stanley Cup wins in history

Every year, the very best take to the ice for one of the most demanding tournaments in all of sports, the Stanley Cup Playoffs. Over a two-month period, the 16 best teams in the NHL do battle to lift that mammoth trophy. Every year, there are shocks, thrills, and some of the best sporting moments you are ever likely to witness.

If you love your sports with a flavor of unpredictability, then this could be the event for you, as there has been no shortage of surprise Stanley Cup winners. This year will be no different, but before we start analyzing who we think will become this year’s NHL Champions, let’s first look back at some of the most memorable Stanley Cup wins in history.

This list isn’t confined to surprise Stanley Cup winners, but instead also focusses on the Stanley Cup outsider wins in the playoffs and some the Stanley Cup biggest shocks. After all, who doesn’t love a good underdog story, and this is one tournament that consistently provides them.

Toronto Maple Leafs vs Montreal Canadiens - 2021

Let’s start off with one of the more recent Stanley Cup outsider wins. The Toronto Maple Leafs went into the 2021 playoffs with high hopes. It seemed liked those hopes were being realized, with the likes of Auston Mathews, Mitch Marner and John Tavares inspiring them into a 4-1 series lead over the Canadiens.

However, it was a case of ‘the same old story’ for a Maple Leafs side that hasn’t got past round one of the post-season since 2004. It was a series full of drama too, as Montreal needed two overtime wins after going down 3-1 in games. In the decider, it was goaltender Cory Price who was the hero, making a total of 29 saves to deny Toronto.

It was a memorable series win for a Montreal side that hadn’t faced the Leafs in the playoffs since 1979. The only other time the two teams went to a game seven, saw Toronto come out on top in 1964.

The Leafs are a much better side than their post-season record suggests.

Los Angeles Kings vs Edmonton Oilers - 1982

You know a playoff series is iconic when one of the games from it has a nickname. The third game from the 1982 semi-finals is one such game. Known as the ‘Miracle on Manchester’, it was the third game in the series between the LA Kings and the Edmonton Oilers. Going into this series, the Kings were massive underdogs as the oilers had some of the best players to ever put a blade on the ice. Amongst their roster were the likes of Wayne Gretzki, Jarru Kuri and Paul Coffey. However, the Kings were a team that defined ‘never say die’. Never was this demonstrated more than it was in game three of the series, with the sides tied at a game each. Here, the Oilers had asserted their dominance and went 5-0 up heading into the third quarter.

This was when the ‘Miracle on Manchester’ was born. The Kings managed to claw the game back to 5-5, sending it to overtime, where they grabbed victory. The momentum from such a monumental comeback helped push them over the line in game four and one of the most memorable series in the history of the Stanley Cup happened.

In the best of five series, the teams were split after the first two rounds. Heading into the third period in the third game the Oilers were up 5-0 and cruising to a victory. The Kings kept chipping away at the Oilers and with five minutes remaining the score was 5-3. Edmonton were handed a five-minute penalty, giving the Kings a power play.

The Kings took advantage and forced the game to extra time before scoring the winner in overtime. Momentum shifted, and the Kings defeated the Oilers again to take the series and one of the most unlikely Stanley Cup outsider wins in hockey history.

Edmonton Oilers vs Detroit Red Wings - 2006

It is the second time that the Oilers has made our list, but this time, they are on the right side of one of the Stanley Cup biggest shocks. Entering this series, the Oilers had not won a playoff series in eight seasons, while the Red Wings were considered the best team in the game. This was demonstrated by an excellent regular season, where they amassed an impressive 124 points.

There were very few reasons to think that the Oilers could get the win over Detroit. On paper, the Red Wings had all the tools to completely dismantle Edmonton, but hockey isn’t played on paper. The Red Wings had one of the best rosters in modern times, with names like Yzerman, Shanahan, Lidstrom, Lang and Chelios being key to their excellent season form.

After four games in this series, the teams were tied, but the Oilers were inspired by their goaltender Dwayne Roloson in Game 5. Then in Game 6, they should amazing grit and determination to twice come from behind and get the series victory. Ales Hemsky was the hero and Edmonton went on to reach the finals that year, where they lost in an epic series against the Carolina Hurricanes.

Toronto Maple Leafs vs Detroit Red Wings - 1942

The sides with the second and third most Stanley Cup wins faced off in the 1942 finals and it was a series full of upsets. Firstly, in terms of seeding, the Leafs were favorites going into the NHL finals.

Thus, the Detroit Red Wings were on the verge of becoming one of the Stanley Cup outsider wins when they went 3-0 up in the series. It wouldn’t have been one of the Stanley Cup biggest shocks, but it certainly would have been surprising if they swept the Canadiens.

However, Toronto’s comeback must be considered one of the Stanley Cup biggest shocks as this comeback looked incredibly unlikely after those first three games. The Leafs looked a completely different side in the next four games, annihilating the Red Wings in one of the most memorable Stanley Cup wins.

To comeback in the way they did with the championship on the line was an amazing achievement for this Toronto Maple Leafs’ team.

New York Islanders vs Pittsburgh Penguins - 1993

The Penguins were going for a three-peat in 1993 and looked unstoppable. Their team included the likes of Mario Lemieux, Ron Francis and Jaromir Jagr and they entered the Stanley Cup playoffs with incredible form.

The Islanders weren’t a bad team, entering the playoffs as the No.3 seed, but not many gave them hope against the Penguins. Their hopes looked to go from bad to worse after their best player Pierre Turgeon was ruled out of the series because of injury.

Somehow, the islanders managed to bring this series to a game seven, where David Volek would famously score and end the Penguins run of Stanley Cup victories. There hasn’t been much to shout about for Islander fans since that famous victory, but they will always have the memories of 1993, when they created one of the Stanley Cup biggest shocks.

Stanley Cup 2022 picks and predictions

The 2022 Stanley Cup playoffs are officially upon us - and we've got some expert Nashville Predators @ Colorado Avalanche picks or you. Take a look and see who our handicappers are picking in tonight's game.

Find the best Stanley Cup 2022 expert free picks

We've covered all bases with our Stanley Cup coverage this year. If you think you're ready to take the advice of our expert hockey handicapper, you can check out our free Stanley Cup picks.

Stanley Cup winners 1981 - 2021

YearTeam
2021Tampa Bay Lightning
2020Tampa Bay Lightning
2019St. Louis Blues
2018Washington Capitals
2017Pittsburgh Penguins
2016Pittsburgh Penguins
2015Chicago Blackhawks
2014Los Angeles Kings
2013Chicago Blackhawks
2012Los Angeles Kings
2011Boston Bruins
2010Chicago Blackhawks
2009Pittsburgh Penguins
2008Detroit Red Wings
2007Anaheim Ducks
2006Carolina Hurricanes
2005Season canceled due to the 2004–05 NHL lockout
2004Tampa Bay Lightning
2003New Jersey Devils
2002Detroit Red Wings
2001Colorado Avalanche
2000New Jersey Devils
1999Dallas Stars
1998Detroit Red Wings
1997Detroit Red Wings
1996Colorado Avalanche
1995New Jersey Devils
1994New York Rangers
1993Montreal Canadiens
1992Pittsburgh Penguins
1991Pittsburgh Penguins
1990Edmonton Oilers
1989Calgary Flames
1988Edmonton Oilers
1987Edmonton Oilers
1986Montreal Canadiens
1985Edmonton Oilers
1984Edmonton Oilers
1983New York Islanders
1982New York Islanders
1981New York Islanders

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