The 15 Worst NHL Teams To Win The Stanley Cup

Hockey fans and pundits always love to say that the Stanley Cup is the hardest trophy in sports to win, and I tend to agree with that statement. When you combine the physicality of hockey, with the long 82-game season, along with four best-of-seven rounds and the abundance of X-factors in hockey, winning a Stanley Cup is an incredible accomplishment.

In the NFL, a 9-7 or 10-6 team can get hot at the right time and ride through January to the Super Bowl. Upsets are more likely to occur in a one-game playoff. In baseball, less Cinderella teams make it due to the 162-game season separating pretenders from contenders. In the NBA, if you have the superstars, you'll get it done.

It's hard to decide who should make a list of the 15 worst Stanley Cup winning teams. After all, if it's the hardest trophy in sports to win, how can a bad team win it? Well, the truth is, not many teams on this list were actually bad. They were just a little underwhelming in their performance that particular year, yet were the last team standing.

Other factors taken into this list are how the team that won did in subsequent years. Did they prove to be a fluke or did they sustain their success?

Some fans may take offense to finding one of their team's Stanley Cup winners on this list, but I say you should feel the opposite. Take pride in the fact that your team managed to win it all despite not being at their best. Plus, nobody can take away a championship from you, so no need to get riled up.

Here are the 15 'worst' teams to win a Stanley Cup.

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15 1990 Edmonton Oilers

via theyardbarker.com

Most people assumed that when Wayne Gretzky was traded, the Oilers' days of winning the Stanley Cup were over. Well, the Oilers managed to pull one last hurrah in 1990, upsetting the Boston Bruins in five games to win their fifth Stanley Cup.

Now, a team featuring the likes of Mark Messier, Jari Kurri, Adam Graves certainly doesn't sound like a bad one, but this was also an Oilers team void of Gretzky, Paul Coffey and Grant Fuhr, key players from their 80s dynasty.

The 1989-90 Oilers managed to win just 38 games that season, but luckily the Campbell Conference was weak that year, with Calgary topping the bunch with 42 wins.

The Oilers rode the magic carpet to the Stanley Cup on the back of Bill Ranford, who would win the Conn Smythe trophy.

14 1993 Montreal Canadiens

via montrealgazette.com

Since 1979, the Montreal Canadiens have won only two Stanley Cups and neither of their two Cup winners since can compare to their legendary teams of the 50s, 60s and 70s. While 102 regular season points is nothing to sneeze at, they were far from the most talented team in the NHL. Heck, they weren't even the most talented team in their division.

Thanks to amazing goaltending and favorable matchups in the playoffs, the Habs managed to win 10 overtime games. After overcoming a 2-0 series deficit against Quebec, they avoided a second round matchup with the Bruins, who had their number in previous years. Then, the Islanders took out the two-time defending champion Penguins, who were prime picking for Montreal. Finally, the Kings took out a very strong Leafs team, and the Kings came off a grueling seven-game series as well.

Fortune was definitely on the Habs' side for this Cup run, but hey, anybody would take that.

13 1949 Toronto Maple Leafs

via icehockey.wikia.com

In the interest of historical balance, we're going to be going way back to the original six era for some of our choices. The 1948-49 Toronto Maple Leafs paled in comparison to the Red Wings, Bruins and Canadiens. While records were inevitably going to be subpar in a league of six teams, where four made the playoffs, it's still something when a team with a losing record wins it all.

The 1948-49 Leafs finished with a record of 22-25-13, which was still good enough to beat out Chicago and New York for the final playoff spot. From there, the Leafs managed to get hot at the right time. They took out the Bruins in five games, before sweeping the favored Red Wings in the Cup Final. This marked the first time in NHL history that a team won three straight Stanley Cups.

12 1934-35 Montreal Maroons

via icehockey.wikia.com

The Maroons were in fact a team with a winning record in the 1934-35 season, as they posted a 24-19-5 regular season, good enough for second in the league's Canadian Division. Back then the playoffs began with two rounds, consisting of two games each, and winners were decided on goal differential, much like UEFA's Champions League tournament in soccer.

The Maroons were scoreless after two games with Chicago in the opening round and advanced after an overtime winner by Baldy Northcutt (gotta love that name). From there, the Maroons beat the Rangers by an aggregate score of 5-4, advancing to the Final. There, they would upset the first seeded Leafs, sweeping them in three straight.

11 1945 Toronto Maple Leafs

via thehockeynews.com

The 1944-45 season was supposed to be all about the Montreal Canadiens. Maurice Richard enjoyed a breakout season, scoring 50 goals in 50 games. The Habs finished with a 38-8-4 record and seemd poised to win their second straight Stanley Cup. Nobody really took the Leafs seriously, who barely squeaked over .500 with a 24-22-4 record. The Leafs drew Montreal in the semifinals and somehow took the first two games at the Montreal Forum. They eventually won in six games on the back of goalie Frank McCool, who shut down the juggernaut Habs.

The Leafs would then upset the Red Wings in seven games, with McCool proving why he won the inaugural Calder Trophy for Rookie of the Year. This really was an era where you couldn't count any team out come playoff time.

10 2006 Carolina Hurricanes

via canescountry.com

I was torn whether to put this Carolina team on the list, because when you look back at the roster, they were pretty solid all the way through. Rob Brind'Amour was a very experienced NHL player and was a great captain to the Hurricanes. They had a young budding star in Eric Staal, who had broken out that season and veterans Cory Stillman and Mark Recchi proved to be great additions to the team.

However when looking at their Stanley Cup run, the Canes seemed to get all the breaks. In their first round series, down two games to none to Montreal, Justin Williams caught captain Saku Koivu with a high stick. Koivu was left with a bloody eye and almost lost his vision from the stick, but somehow the play went unpenalized. The Canes took Game 3 and without the Habs' captain, Carolina took control of the series.

In their Conference Finals matchup with Buffalo, the Sabres lost four of their starting six defencemen due to injury.

In Game 1 of the Stanley Cup Final, the Canes faced the Cinderella Edmonton Oilers, who then lost their star goaltender Dwayne Roloson for the series. Facing an unknown Jussi Markanen in nets, the Canes still took seven games to beat Edmonton. It's highly doubtful this team would have beaten the 2005-06 Red Wings if the Oilers hadn't knocked them off.

9 1986 Montreal Canadiens

via allhabs.net

The 1985-86 Habs still had several pieces from their Stanley Cup runs of the 70s, but by this point, the Habs' dominance over the NHL was over. Sure, they still had Bob Gainey and Larry Robinson, and had also seen new stars emerge like Mats Naslund, Guy Carbonneau and Chris Chelios, but this team needed some lucky breaks to take home the Stanley Cup.

First of all, a former third round pick named Patrick Roy came out of nowhere, and went on the run of his life in the 1986 playoffs.

Where people say the Habs really got lucky was what happened on the other side of the playoff bracket. The Flames managed to knock off the dominant Edmonton Oilers in a grueling seven-game series thanks to Steve Smith scoring in his own net.

It's highly doubtful the Habs, who only recorded 87 points that season, would have been able to stop the Oilers in the Cup Final.

8 1992 Pittsburgh Penguins

via sportslogos.net

When looking at the Penguins teams of the early 90s, you might have thought that they were teams that ran roughshod over their opponents during the regular season, but that wasn't the case. Despite having Mario Lemieux, Jaromir Jagr, Kevin Stevens, Joe Mullen, Larry Murphy and Bryan Trottier on the team, the Penguins had a roller coaster 1991-92 season. They recorded just 39 wins and many didn't expect them to repeat as Stanley Cup champions.

This proved to be a case of the team peaking at the right time, as the Penguins eventually managed to sweep their last two series. The Penguins, despite earning just 87 points in the regular season, got home ice advantage in the final two rounds, thanks to the Bruins having just 84 points, while their Stanley Cup Final opponents, the Blackhawks, who also had just 87 points.

7 1997 Detroit Red Wings

via nhl.com

This Red Wings team proved not to be a fluke, as they would win the Stanley Cup in 1998 and 2002 with this same core, but their win in 1997 was a bit surprising. Perhaps it was a case of the Wings having gained valuable experience in previous playoff disappointments, but the 1996-97 team was not the best that this era's Red Wings put on the ice. After a historic 1995-96 season where the Wings finished with 132 points, they finished with just 94, earning 38 wins in the process. They finished 10 points behind the Central Division winners, the Dallas Stars.

It seemed like a showdown between the Stars and the Avalanche was inevitable, but the Stars were upset by the Oilers. The Wings had favorable matchups with St. Louis and Anaheim, before meeting the Avalanche in the Western Conference Finals.

The Wings exercised their revenge for '96 and upset the Avs. In turn, they would sweep the Flyers in the Stanley Cup Final. Of all the Wings teams of the 90s, the 1996-97 one was not the one people expected to win it all.

6 1971 Montreal Canadiens

via habseyesontheprize.com

The Montreal Canadiens had just come off one of their most disappointing seasons in franchise history. After closing out the 60s with five straight Stanley Cup Finals appearances and four championships, the Habs failed to even make the postseason in 1970. An aging Jean Beliveau decided he didn't want to end his career like that and stuck it out for one more season.

The Habs finished with 97 points, which was respectable, but paled in comparison to the Bruins, who snatched 121 points, along with a season goal differential of +192.

All of a sudden, rookie goaltender Ken Dryden came out of nowhere, and helped the Habs knock off the big bad Bruins in the opening round. The Habs would then draw a favorable matchup with the Minnesota North Stars, before eking out a Finals win over Chicago in seven games.

The Habs were at an awkward time here of transitioning from one era to the next and nobody expected them to win it.

When asking many old-time Habs fans which Cup win was their favorite though, many will point to this one.

5 1995 New Jersey Devils

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The 1995 New Jersey Devils were coming off a season in which they had fallen to the Rangers in Game 7 of their Eastern Conference Finals series. The 48-game regular season (caused by a lockout) opened the door for unusual suspects to squeak into the playoffs and perhaps the Devils simply hadn't found their stride during the season. After all, they only won 22 games, finishing with a record of 22-18-8.

Come playoff time though, the Devils' notion of hockey proved to be highly effective. Head coach Jacques Lemaire introduced the dreaded trap to the game of hockey and even some of the league's biggest offensive juggernauts in Pittsburgh, Philadelphia and Detroit just couldn't slow it down. It's quite possible that this 1994-95 Devils team would have missed the playoffs if the season had been 82 games.

4 1967 Toronto Maple Leafs

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Hey Leafs fans, I'm not trying to take anything away from you. You should be as proud as you can be of this 1967 team, because despite being inferior in talent, they managed to shock the hockey world and take home the Stanley Cup.

The Leafs won less than half their games that season, recording just 32 wins in 70 games. Many expected the twp time defending champion Canadiens to take the Stanley Cup in what would be the last season of the original six era. Somehow the Leafs upset the top-seeded Blackhawks, then defeated the Canadiens in six games to win their 13th Stanley Cup.

As we know, that was their last one, but it sure was a shocking one. With the Habs having won the '65, '66, '68 and '69 Stanley Cups, this Leafs team spoiled the chances of another five-peat for the Habs.

3 2012 Los Angeles Kings

via hockeygods.com

Considering how the Los Angeles Kings came back the following season to reach the Western Conference Finals, then won the 2014 Stanley Cup, I had trouble deciding whether to include them on this list.

The Kings became the first no.8 seed to win the Stanley Cup in NHL history. The Kings loaded up at the trade deadline that year, acquiring Jeff Carter, after having already traded for Mike Richards before the season.

Once the playoffs started, the Kings sure didn't play like underdogs, as they took out the Presidents' Trophy winning Canucks in five games, then swept the Blues. They convincingly beat the Coyotes in a five game series, before taking six to beat the Devils.

Los Angeles quite simply dominated that postseason and it was incredibly shocking to think they were a fringe playoff team.

2 1934 Chicago Black Hawks

via nhl.com

The 1933-34 Chicago Black Hawks (the team was spelled in two words back then), were not only unimpressive with just 20 wins on the year (20-17-11) but they also scored the fewest goals and allowed the fewest, making them one of the more boring teams to watch in the NHL. With only four teams in the American Division though, the Hawks didn't have much competition and thanks to their 11 ties, they beat out the Bruins for the second seed in the division.

Coming back to the aggregate system for the playoffs, they beat the Canadiens by an aggregate score of 4-3 in the opening roud, then the Maroons on a 6-2 aggregate. From there, they upset the division rival Detroit Red Wings in the finals, winning three games to one.

1 1938 Chicago Black Hawks

via cbssports.com

When looking back at every single Stanley Cup winner in history, picking the 1937-38 Black Hawks as the worst Stanley Cup winner was a no brainer. As we know, the NHL wasn't exactly a deep league at the time, and the Black Hawks somehow had a weaker team in their division. Chicago somehow made the postseason despite a paltry record of 14-25-9, which was still sufficient with the Red Wings having won just 12.

Needless to say, the Hawks were expected to quickly ow out to the Montreal Canadiens in the first round, but somehow, they beat the Habs in a best of three. They followed that up by beating the New York Americans in a best of three. They completed their miracle run by knocking out the Leafs in four games in the best-of-five final.

This team will forever remain the worst to win the Cup, because 14 wins today would only happen to an expansion team.

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