Best NHL Teams To Never Win A Cup

Winning the Stanley Cup is hard. It's widely accepted as the most difficult trophy to capture in all of pro sports. You've got 82 regular season games played in 30 different cities all over North America. Fourteen teams don't make it to the playoffs. Once there, a team must win four best of 7 playoff series to win the big prize. Sixteen wins. Of course, it hasn't always been that way. There used to be less teams (a lot less if you go back far enough) and seasons were shorter. The playoff format has changed over the years as well and sometimes it featured series that were best of 5 and even some best of 3s. Sometimes top-seeded teams even earned a bye that sent them straight to the second round. But still, I'm pretty sure it was just as hard in the old days.

This list's title makes it fairly self-explanatory but I will mention a few things. Firstly, that I suppose if you did the research and tallied up wins totals and how far each team actually traveled in the playoffs, you might discover that my list is out of order. That's if we're reducing hockey to simple stats. But we all know there's a lot more to the game than that so trust my amazing instincts and intuition.

Also I'll point out that one rule I had was to only include teams that were at least 5 years removed from a Cup win in either direction. So possible dynasties that were interrupted (see the 1970-72 Bruins who were shocked by Ken Dryden and the Habs in 1971 to break up their chance at 3 straight, the Oilers in 86 and 89, etc.) or were simply drawing to a close (see 1985 Islanders, 1961 Canadiens, etc) won't be seen here. Because those teams DID win cups in that at least most of the same players were present during the championships.

Further to that point I'll just say that I am actually including one glaring exception to the rule just stated above. When we get to it, you will understand why I had to break it that one time.

Here are the absolute best losers in NHL history.

5. St. Louis Blues 1998-2002 (Pierre Turgeon pictured)
Since entering the NHL in its first year of expansion (1967/68), the Blues have been one of the most consistently good teams (some very early appearances in the Final and from 1980 to 2004 they made the playoffs every single season). But a Stanley Cup has eluded them so far. Since the lockout of 2004/05, they've actually been pretty lousy but only a few years before that they were at their very best.

The Mike Keenan years of the mid nineties caused a lot of turmoil and the 1996 acquisition of Wayne Gretzky didn't work out. Their nemesis, the Detroit Red Wings sent them packing from the playoffs as usual and the Great One signed with the Rangers that offseason. By the 98/99 season, superstar and face of the franchise, Brett Hull was gone. But that was ok. Pavol Demitra and Chris Pronger were both coming into their own and Pierre Turgeon, acquired from Montreal the year before, was showing he was quite happy to be the hell out of Montreal. In goal, veteran Grant Fuhr ran out of gas after being overplayed but Roman Turek stepped right in and performed great. And Al MacInnis was...Al MacInnis.

But the damned Wings sent them home again in 98. The 99/00 Blues set a franchise record for wins and points, finishing best in the league with 114 points (thus winning the President's Trophy). Pronger won not only the Norris Trophy but the Hart as well. It seemed like they had finally surpassed Detroit. So then what happened? They were stunned in a 7 game upset in the first round against the eighth-seeded San Jose Sharks.
The next year featured an out of nowhere 40 goal season from scorer Scott Young and they at least made it to the second round but as usual, that was as far as they'd go.

By the 01/02 season, Turgeon was gone but he was ably replaced by two Americans: sniper Keith Tkachuk and playmaker Doug Weight. They helped keep the Blues powerful until 2004 but the playoff failures continued. As balanced and talented as the Blues were from 1998 to 2004, they never once made it past round two.

4. Boston Bruins 1987-1994 (Adam Oates pictured)
After years of, to use the proper term, sucking, the Bruins were an absolute powerhouse in the early and middle seventies featuring teams stocked full of immense talents like Phil Esposito, Ken Hodge, Derek Sanderson and, of course, Bobby Orr. The fact that they only won Cups in 1970 and 1972 speaks volumes about just how amazing the Montreal Canadiens teams of that era were, even stealing a Cup from the Bruins in 71 when mostly overmatched.

By the eighties the Bruins had changed quite a bit but they remained a strong team, making the playoffs every year. Ray Bourque was probably the best defenceman ever after Orr (sorry, Doug Harvey) and, just like Orr, he was Bruins' property. Along with guys like Brad Park and Rick Middelton they were pretty good. But in 1986 the Bruins were the beneficiaries of one of the most lopsided trades in league history, landing Cam Neely (AND a first round pick) for Barry Pederson ("who"? - exactly).

As Neely became one of the best goal scorers and power forwards in the game, the Bruins went from pretty good to really good. In 1988 they made it to the Final. But this was the eighties and you know what that means - the first half belonged to the Islanders and the second to the Oilers. And it was the Oilers that the Bruins now faced. They were swept in four games (well, four and a half - look it up, it's cool). 1990 saw the Bruins meet the now Gretzky-less Oilers in the Final once again. This time they took one game but still were beaten.

Ex-Oiler goalie Andy Moog was a great stopper for the Bruins and the cerebral Craig Janney's slick passing skills only further complimented Neely's scoring ability. Bourque, their leader, remained one of the league's elite blueliners. And 1990 was to be the mighty Oilers' final Cup. The problem for the Bruins was, they'd gone from coming up short twice against one dynasty team in the West to having to deal with an emerging one in their own conference, the East. Ron Francis proved to be the final needed piece for the puzzle that was Mario Lemieux's Pittsburgh Penguins. In 1991 and 1992, the Bruins made it to the Conference Finals. Both times they were met and defeated by the Penguins, who would go on the win the Cup both times as well.

1993 saw one of the most shocking playoff upsets of all time with the Penguins, in their bid for a third straight Cup, being knocked out in the first round by the plucky New York Islanders (and their only real star, Pierre Turgeon was hurt and couldn't play!) You'd think this meant that the way was now clear for the Bruins, who had finished second in the league after the Penguins. But no, they were out even faster - having been swept by the Buffalo Sabres.

Players like Adam Oates, an even better playmaker than Janney, and super rookie Joe Juneau (who would decline in every season) kept the Bruins powerful in the early nineties but playoff success still didn't happen. A devastating injury eventually ended Neely's fantastic career far too soon. He'd managed an astonishing fifty goal season in 93/94 despite only playing FORTY-NINE games (and he actually hit 50 in his 44th game) but missed the playoffs altogether. After that season the Bruins would slide into mediocrity, eventually missing the playoffs in the 96/97 season. It was the first time in 30 years they wouldn't play into the spring.

3. Toronto Maple Leafs 1992-1995 (Doug Gilmour pictured)
Favouritism? You decide. The Leafs were a very strange up and down team throughout the eighties. But the ups hardly amounted to anything besides frustration and the downs were extreme. In 1990 that bastard Harold Ballard finally died and things immediately started looking up for the Blue and White and their fans even though their playoff appearance that year lasted only five games. They'd also miss the post season in the next two seasons.

But with Ballard at long last gone it was Steve Stavro who was in charge and he wasn't a crazy control freak like the previous owner (I'll have to do a list on the biggest assholes in pro hockey just so I can rant some more about Ballard) and knew he should put the team in the hands of people who actually knew something about hockey. He hired Cliff Fletcher, the man who'd built the 1989 Stanley Cup champion Calgary Flames. By the time the 92/93 season (which was INSANE - I could write several lists dedicated to it) started, Fletcher had taken drastic measures to rebuild the Leafs into an immediate contender. This was of course highlighted by the massive 10-player trade with his old team the Flames. The crown jewel of this blockbuster move was the Leafs landing Doug Gilmour, who was about to become one of the biggest heroes in the history of the franchise. Fletcher also hired Pat Burns as head coach.

Incumbent hero and team captain, Wendel Clark played 66 games that season which was a lot for him (his kamikaze playing style led to tons of injuries) and his most in many years. And yet he was a disappointment, scoring only 17 goals and 39 points. But this was glossed over by the fact that it was still an extremely successful regular season for the team as a whole. The Leafs finished with a then franchise record 99 points. Because while Clark disappointed, Gilmour skyrocketed, scoring 127 points (team record) with 95 assists (team record). He also won the Selke Trophy that year as the game's top defensive forward (impressive plus/minus of 32) and finished second in Hart Trophy (league MVP) voting.

If you're wondering how Gilmour racked up so many assists with Clark finding the back of the net only 17 times, the answer lies with another move by Fletcher. As rookie goaltender Felix Potvin proved he was the real deal with his absolutely stellar play highlighted by flashy, acrobatic saves (he probably would have won the Calder Trophy if not for Teemu Selanne's insane 76-goal season), Fletcher found he could afford to move veteran goalie, Grant Fuhr and get something substantial in return. That something was scoring winger, Dave Andreychuk, who meshed perfectly with Gilmour, scoring 25 goals in the 31 games he played after arriving. This would give him 54 in total. It was the first time he reached the 50-goal mark and it made him one of the very, very few players in NHL history to be traded during a 50-goal season.

I know I'm being wordy so let's fast forward to the playoffs. There, the Leafs dispatched the Red Wings and then the Blues, both in dramatic seven game series. At the same time as providing offence, Gilmour checked Steve Yzerman and then Brett Hull, keeping the stars from lighting up the Leafs. Led by Gilmour, the Leafs were playing out of their minds. They seemed to be a team of destiny. When they reached the Conference Finals to face the Los Angeles Kings, most fans were already looking ahead to the Final where a possible matchup with the Montreal Canadiens awaited.

But it's very unwise to overlook Wayne Gretzky. Like Clark, 99 had had a somewhat disappointing regular season. But the playoffs are what really matters. In another dramatic, back and forth series, the Leafs had the upper hand heading into LA for game 6 with the chance to eliminate the Kings. It was the second-most heartbreaking game I've ever experienced. Clark, who was making up for his season with an outstanding playoffs, scored a hat-trick. With the score tied late in the third period, Gretzky high-sticked Gilmour in the face. It was blatant. It was obvious. It even cut Gilmour so it should have been a four minute penalty instead of a regular two minute minor. Referee Kerry Fraser missed it. Moments later, Gretzky himself scored the winning goal.

Game 7 was back in LA. Gretzky scored a hat-trick of his own and the Kings prevailed, ending the Leafs' best run since 1967. Gretzky has said the best game he ever played was a 5-assist performance against the Russians in the 1987 Canada Cup. He's also said a short-handed overtime game-winner against the Flames in the 1988 playoffs was the greatest goal he ever scored. But for best playoff series, he said it was that one against the Leafs. The best series ever played by the best player ever and he had to save it for my Leafs.

The Leafs had another great season the next year and made it back to the Conference Finals again. Another 100 points for Gimour. Another fifty goals for Andreychuk. Clark bounced back with a career-high 46. But they were eliminated by Trevor Linden, Pavel Bure, Kirk MacLean and the rest of the Vancouver Canucks.

The lockout shortened 94/95 season saw the departure of Clark and the arrival of Mats Sundin. The young Swede was a point a game player in the season and dominant in the playoffs but Ed Belfour worked his magic to help the Chicago Blackhawks knock off the Leafs in the first round. A few years of mediocrity and playoff misses would follow as stars like Gilmour, Andreychuk and Dave Ellet were traded away. From 1998 to 2004 the Leafs would again be a strong team and they made it to the Conference Finals again in 1999 and 2002 but the early to mid nineties teams just had a certain magic about them that gets them on this list.

2. Philadelphia Flyers of the 80s (Brian Propp pictured)
Using a unique blend of skill and toughness the Flyers of the seventies managed to win back to back Cups in 1974 and 75. In a decade ruled by the Guy Lafleur-led Canadiens and the Bobby Orr Boston Bruins, this was no small achievement. By the eighties the Flyers no longer possessed talent or toughness as great as what they'd had. But they were still good. Damn good.

Although their teams in the eighties didn't feature any dominant superstars like they'd boasted before, they were just top to bottom good. Players like Brian Propp, Tim Kerr, Ken Linesman, Mark Howe and Dave Poulin performed wonderfully and made the Flyers a force to be reckoned with throughout the decade.

In the 1980 Stanley Cup Final, seventies veterans Bobby Clarke, Reggie Leach and Bill Barber, who were all instrumental in their Cup wins, almost got it done again but they wound up falling to the New York Islanders in six games. Everyone knew the Isles were good by that season, even before the playoffs, but no one really knew how good. They would win 4 Cups in a row from 1980 to 83. But it was really only that first year that they were the problem for the Flyers. Throughout the first half of the decade, the Flyers would make early playoff exists, losing to teams they probably should have beaten.

By the 84/85 season, the players I mentioned at the top were entering their primes. And goalie Pelle Lindbergh was becoming a star. The Flyers finally made it back to the Final that year. Of course they ran into the Edmonton Oilers who had taken the torch from the Islanders the year before, defeating them for the Cup and becoming the decade's new dominant team. The Flyers actually managed a very impressive 4-1 win in Game 1 but the Oilers would storm back to win the next four straight and capture their second Cup.

Early into the next season, Lindbergh would die in a car crash. But the Flyers still managed to carry on as an elite team without him.

In 1987, led by a sublime performance from rookie goalie Ron Hextall, they would meet the Oilers in the Final once again, only this time they took them all the way - seven games - before losing once more. Hextall was so good he still won the Conn Smythe.

How good were the Flyers of the eighties? Well, in the 79/80 season they went on an unbelievable run of 25-0-10 - by far the longest undefeated streak in league history. They had 53 wins in 84/85 and then again in 85/86. That year Kerr scored 58 goals and the defence pairing of Howe and Brad McCrimmon led the league with eye-popping plus/minuses of 85 and 83 respectively. In his rookie season (86/87) Hextall won the Vezina Trophy before his Conn Smythe performance in the playoffs. He'd also become the first goalie in history to score a goal by shooting the puck into the opposing net. He did this in the regular season and then later in the playoffs as well. Propp would top 90 points four different times. Kerr would score at least 54 goals for four straight seasons and only injuries kept him from doing it again. Howe, an offensive defenceman, would average over 60 points a season since arriving in 1982/83 till decade's end.

By 1988 and 89, the Flyers weren't quite as formidable as they'd been but they still made the playoffs each year. Looking back on the decade you'd have to think they were good enough to have perhaps won multiple Cups and would have had 3 if not for two different powerhouse dynasties.


1. Toronto Maple Leafs 1933-1941 (Joe Primeau pictured)
We've reached the top of the list. And here's the big exception to my five-year rule. In the midst of the Great Depression, the city of Toronto was actually seeing some progress and modest prosperity. Using some impressive economic smarts, team owner Conn Smythe built the fabled Maple Leaf Gardens in only six months in 1931. He bought land on the northwest corners of Carlton and Church streets for well under market value then convinced unionized construction workers to accept preferred shares in the Leafs instead of hourly wages. The building was constructed for $1.5 million. Despite the economic climate, the Gardens drew good crowds. Dubbed the "Carlton Street Cashbox", there was boxing, basketball, concerts and wrestling.

And there was the Leafs. The city fell in love with them and flocked to see them. Smythe, a visionary for his time, had every game broadcast on radio (by now legendary voice Foster Hewitt). In very short order, the Leafs had become Canada's team.

They played like it too. In their very first season in the Gardens, 1931/32, the Leafs won the Stanley Cup. They were a speedy, high-scoring group with superstar defenceman, King Clancy as the centrepiece. Two other Hall of Famers were on the Leafs' defence as well - Hap Day and tough as hell Red Horner. Opposing forwards had no fun playing against those guys. Up front they were led by the famous Kid Line which included centre Joe Primeau with Charlie Conacher and Busher Jackson on the wings. In the Final, the talented lineup defeated the New York Rangers in three straight games (best of five). With a young hungry team assembled, the future looked bright for the Leafs. They were sure to be a strong team for years to come. And they were. They appeared in the Final in 1933, 35, 36, 38, 39 and 40. They lost every single one.

The possible reasons for such unheard of failure are intriguing. Something certainly worth noting is that during the 1933 regular season, forward Ace Bailey, emerging as a great player, was injured so severely that he almost died. Eddie Shore of the Boston Bruins - a superstar but also an incredibly violent and ill-tempered one - mistook Bailey for Clancy and hit him from behind. Hard. Bailey fell and bashed his head off the ice, fracturing his skull. Surgery saved his life but his hockey career was over. The team soldiered on and played through an exhausting playoffs complicated further by a very cruel schedule. By the time they met the Rangers in the Final, they had nothing left and lost three games to one.

Another possible factor was Smythe's decision to get rid of goaltender Lorne Chabot, one of the great forgotten goalies of the NHL and the man who had backstopped their Cup win in 1932. Smythe disapproved of Chabot's lifestyle even though his play was stellar. So out he went. Former Montreal Canadiens great, George Hainsworth replaced him but it's likely that he was past his prime by then.

In 1935 the Leafs finished first in the regular season standings for the third season in a row. Things finally seemed to be going right again as they cruised through the playoffs. They met Montreal in the Final. No, not the Canadiens but the Montreal Maroons (it's a misconception that the Maroons were a previous incarnation of the Habs but this isn't the case. The two teams coexisted for 15 years). The Leafs were heavily favoured in the matchup. They lost in three straight. The next year they were back in the Final again, only to lose to the Detroit Red Wings.

By the next year, Smythe knew some changes were needed. Day, Clancy and Hainsworth were all sent packing. Joe Primeau retired somewhat prematurely. So in came Turk Broda, Syl Apps and Gordie Drillon. All good players, particularly Apps and Broda who have to be considered among the greatest Leafs of all time. They finished first in their division for the 37/38 season and rolled through the playoffs to reach the Final once again. They met the Chicago Black Hawks there (before the seventies, the name was separated into two words). A team that had finished a dismal 14-25-9. Even though the Hawks went up two games to one in the series, they were such underdogs that the NHL didn't even bother to ship the Stanley Cup to Chicago for Game 4. So when they won that game I guess it was pretty awkward to not have the Cup present to give to them. Leafs lose again.

The 1939 Final was the first ever to be a best of seven series. That didn't help the Leafs any as the Bruins beat them in five. They managed only 6 goals in the entire series. Further insult to injury came when the Stanley Cup-winning goal was scored by Flash Hollett. Hollett had played for the Leafs in the 34/35 season showing a great scoring touch with 10 goals and 26 points in 48 games. But early into the following season he was gone, dealt away by Smythe because of some stupid personal feud between the two. He went on to be one of the highest scoring defencemen of his era.

The cycle of futility was complete when the Leafs fell to the Rangers in 6 games in the 1940 Final. From 1931/32 to 1939/40 the Leafs were a powerhouse, always finishing high in the regular season and making it to the Final an amazing 7 times. And they only came away with one Cup.

The forties would be a great time for the Leafs. Between 1942 and 1951 they were in the Final 6 times. They won every time, becoming the NHL's first true dynasty. But in the thirties the Leafs were arguably just as good and will always be remembered as the dynasty that never was. By those that actually remember anyway.