Worst Underachieving Teams in NHL History

The NHL is made for upsets, and some mighty good teams have paid the price.

Worst Underachieving Teams in NHL History

The 1996 Detroit Red Wings lost in the playoffs after a record-breaking regular season.

Puckheads like to brag that the Stanley Cup is the hardest trophy to win in the four major North American pro team sports. Let us explain.

Because the NHL features two seasons in one — the more finesse regular season followed by the more intense and physical playoffs — participants have to be twice as good and lucky to survive both. No league has less of a home advantage. No sport has more random bounces. Only the NBA has as many as 16 postseason teams. And no sport is more physical with a higher attrition rate than the NHL. Sorry, NFL, you’re a close second.

All of these factors are conducive to skewed results in the NHL postseason, where intangibles such as grit and puck luck can neutralize sheer talent. In the NBA, major upsets happen about as often as Don Cherry wears a navy blue shirt. On the ice, they happen all the time. And the more upsets there are, the more really good teams are on the wrong side of the handshake line.

Some great NHL teams never get to hoist the Stanley Cup. These are the best of the worst underachieving teams in NHL history.

Note: The rankings are based on points total, goal differential, Simple Rating System (a combination of average goal differential and strength of schedule, per Hockey Reference), the eye test and whatever the heck else we feel is pertinent.

25. 1989 Montreal Canadiens

Montreal Canadiens right wing Russ Courtnall

Record (league rank): 53-18-9 (2nd of 21)

Goals differential (league rank): +97 (2nd)

SRS (league rank): 1.16 (second)

Head coach: Pat Burns

Fab five: Goalie Patrick Roy, defenseman Chris Chelios and Petr Svoboda, forwards Mats Naslund and Bobby Smith

Where they failed: Lost to Calgary Flames (4-2) in Stanley Cup Final

Bottom line: This Habs team dominated in the regular season, steamrolled through the postseason and had a 2-1 advantage in the championship round. But Montreal never a got a firm grasp on glory.

The Canadiens' undersized front line wore down against the bigger, more physical Flames defense as the series progressed.

And it failed to score more than two goals against goalie Mike Vernon in any of the next three games.

24. 1986 Philadelphia Flyers

Philadelphia Flyers goalie Darren Jensen

Record (league rank): 53-23-4 (2nd of 21)

Goals differential (league rank): +94 (2nd)

SRS (league rank): 1.17 (2nd)

Head coach: Mike Keenan

Fab five: Goalie Ron Hextall, defenseman Mark Howe and Brad McCrimmon, forwards Tim Kerr and Brian Propp

Where they failed: Lost to Edmonton Oilers (4-3) in Stanley Cup Final

Bottom line: The Flyboys did well to overcome a 3-1 deficit in the final round, but this one-line team lacked the firepower and fresh legs to close the deal against the ubertalented Oilers on the road.

It took them 19 games to get through the first three rounds.

23. 1981 Montreal Canadiens

Montreal Canadiens right wing Chris Nilan

Record (league rank): 45-22-13 (3rd of 21)

Goals differential (league rank): +100 (1st)

SRS (league rank): 1.19 (1st)

Head coach: Claude Ruel

Fab five: Goalie Richard Sevigny, defenseman Brin Engblom, Rod Langway and Larry Robinson, forward Steve Shutt

Where they failed: Lost to Edmonton Oilers (3-0) in round one

Bottom line: A bunch of 19-and 20-year-olds shocked the heavily favored Habs out of the gate, and the Ruel era came to a sudden and unceremonious end.

Some kids named Anderson, Coffey, Gretzky, Kurri, Lowe and Messier did the honors.

Sacré bleu!

22. 2006 Ottawa Senators

Ottawa Senators Mike Fisher and Chris Phillips

Record (league rank): 52-21-9 (2nd of 30)

Goals differential (league rank): +103 (1st)

SRS (league rank): 1.18 (1st)

Head coach: Bryan Murray

Fab five: Goalie Dominic Hasek, defenseman Wade Redden, forwards Daniel Alfredsson, Dany Heatley and Jason Spezza

Where the failed: Lost to Buffalo Sabres (4-1) in Eastern Conference semifinals

Bottom line: We're talkin’ about the team with Dominik Hasek here, the one that was headed for a deep postseason run before a groin injury suffered in the Winter Olympics sidelined him for the rest of the season.

Backup Ray Emery acquitted himself well, but he couldn’t prevent a trio of one-goal losses in the semis.

And The Dominator never played another game with the Senators again.

21. 2019 Tampa Bay Lightning

Tampa Bay Lightning center Steven Stamkos

Record (league rank): 62-16-4 (1st of 30)

Goals differential (league rank): plus 103 (1st)

SRS (league rank): 1.21 (1st of 30)

Head coach: Jon Cooper

Fab five: Goalie Andrei Vasilevskiy, defenseman Victor Hedman, forwards Nikita Kucherov, Brayden Point and Steven Stamkos

Where they failed: Lost to Columbus Blue Jackets (4-0) in round one

Bottom line: The runaway President’s Trophy winner was KO’d by an opponent that had 30 fewer points in the regular season and never won a playoff series in their history.

Riddle me this, girls and boys: How can a group this physically talented be so character-flawed at the same time?

20. 1972 Montreal Canadiens

Record (league rank): 46-16-16 (3rd of 14)

Goals differential (league rank): +102 (3rd)

SRS (league rank): 1.21 (3rd)

Head coach: Scotty Bowman

Fab five: Goalie Ken Dryden, defenseman J.C. Tremblay, forwards Yvan Cournoyer, Jacques Lemaire and Frank Mahovlich

Where they failed: Lost to New York Rangers (4-2) in East Division quarterfinals

Bottom line: How loaded was the East Division this season? So loaded that a roster of 10 Hall of Famers couldn’t get out of the first round.

The 109-points Rangers team that did the deed also appears on this list.

19. 1976 New York Islanders

New York Islanders left wing J.P. Parise and right wing Ed Westfall

Record (league rank): 42-21-17 (5th of 18)

Goals differential (league rank): plus 107 (3rd)

SRS (league rank): 1.26 (3rd)

Head coach: Al Arbour

Fab five: Goalies Glenn Resch and Billy Smith, defensemen Denis Potvin and Jean Potvin, forward Bryan Trottier

Where they failed: Lost to Montreal Canadiens (4-1) in league semifinals

Bottom line: This team was better than its record in a top-heavy division. No fewer than 10 players scored 17 or more goals in the regular season.

It took a 127-point Canadiens team on the cusp of a dynasty to take them out in five games, four of which were decided by one goal.

18. 1974 Chicago Blackhawks

Record (league rank): 41-14-23 (3rd of 16)

Goals differential (league rank): plus 108 (3rd)

SRS (league rank): 1.28 (3rd)

Head coach: Billy Reay

Fab five: Goalie Tony Esposito, defensemen Dick Redmond, Phil Russell and Bill White, forward Stan Mikita

Where they failed: Lost to Boston Bruins (4-2) in league semifinals

Bottom line: Only Cain treated Abel worse than Phil Esposito did his brother Tony throughout their careers.

The defensive-minded Blackhawks attempted to beat Espo and company at their own game in the semis, only to be lit up for nearly five goals per start, more than twice their average in the regular season.

Chalk this loss up to a really bad matchup.

17. 1977 Philadelphia Flyers

Philadelphia Flyers goalie Bernie Parent

Record (league rank): 48-16-16 (2nd of 18)

Goals differential (league rank): +110 (2nd)

SRS (league rank): 1.27 (2nd)

Head coach: Fred Shero

Fab five: Goalie Bernie Parent, defensemen Tom Bladon and Andre Dupont, forwards Bobby Clarke and Rick Macleish

Where they failed: Lost to Boston Bruins (4-0) in league semifinals

Bottom line: This was a Stanley Cup-caliber team everywhere except between the pipes, where at 31, Bernie Parent was the postseason MVP of old no longer.

The homies coughed up nine goals in a pair of overtime losses to open the semis, and it wasn’t long before the Bruins got revenge for their Stanley Cup Final setback of three years earlier.

16. 1951 Detroit Red Wings

Record (league rank): 44-13-13 (1st of six)

Goals differential (league rank): +97 (1st)

SRS (league rank): 1.16 (1st)

Head coach: Tommy Ivan

Fab five: Goalie Terry Sawchuk, defenseman Red Kelly, forwards Sid Abel, Gordie Howe and Ted Lindsay

Where they failed: Lost to Montreal Canadiens (4-2) in round one

Bottom line: The defending Stanley Cup champs were 8-4-2 against the third-place Habs in the regular season. Can you say "o-ver-con-fi-dent"?

The Winged Wheels were stunned in the first two games at home — 3-2 in four overtimes and 1-0 in three overtimes — and the monstrous upset was soon in the books.

15. 1985 Philadelphia Flyers

Philadelphia Flyers goalie Pelle Lindbergh

Record (league rank): 53-20-7 (1st of 21)

Goals differential (league rank): +107 (1st)

SRS (league rank): 1.22 (2nd)

Head coach: Mike Keenan

Fab five: Goalie Pelle Lindbergh, defenseman Mark Howe and Brad McCrimmon, forwards Tim Kerr and Brian Propp

Where they failed: Lost to Edmonton Oilers (4-1) in Stanley Cup Final

Bottom line: Forget the final series. Metrics say this is the fifth-best team in franchise history.

The Flyboys rolled through the regular season and first three rounds of the playoffs, only to run into Wayne Greatly and the Oilers machine at the height of their dynastic powers.

That the champs dominated the last four games by a combined 20-10 score said more about their greatness than anything else.

14. 1975 Buffalo Sabres

Record (league rank): 49-16-15 (1st of 18)

Goals differential (league rank): +114 (2nd)

SRS (league rank): 1.35 (2nd)

Head coach: Floyd Smith

Fab five: Goalie Gary Bromley, defenseman Jerry Korab, forwards Rick Martin, Gilbert Perreault and Rene Robert

Where the failed: Lost to Philadelphia Flyers (4-2) in Stanley Cup Final

Bottom line: The playoffs come down to matchups oftentimes, and this finesse team couldn’t haven’t faced a worse one in the final round than goalie Bernie Parent and the Broad Street Bullies.

The Sabres scored four goals in four losses.

Fine print: The Flyers claimed the home-ice tiebreaker as a result of two more wins in the regular season.

13. 1980 Buffalo Sabres

Record (league rank): 47-17-16 (2nd of 21)

Goals differential (league rank): +117 (1st)

SRS (league rank): 1.39 (1st)

Head coach: Scotty Bowman

Fab five: Goalie Don Edwards, defensemen Jim Schoenfeld and John Van Boxmeer, forwards Danny Gare and Gilbert Perreault

Where they failed: Lost to New York Islanders (4-2) in league semifinals

Bottom line: After seven wins in their first eight playoff games, the Adams Division winners met their match against the more playoff-tested Islanders in the next round.

The killer: A 2-1 loss in double overtime in Game 2 at The Aud.

12. 1978 New York Islanders

New York Islanders right wing Mike Bossy and left wing Clark Gillies

Record (league rank): 48-17-15 (3rd of 18)

Goals differential (league rank): +124 (2nd)

SRS (league rank): 1.47 (2nd)

Head coach: Al Arbour

Fab five: Goalie Glenn Resch, defenseman Denis Potvin, forwards Mike Bossy, Clark Gillies and Bryan Trottier

Where they failed: Lost to Toronto Maple Leafs (4-3) in league quarterfinals

Bottom line: No doubt this young, talented team had enough firepower to make a serious postseason run — five forwards scored 30 goals or more — but it still lacked the poise and testosterone to get it done.

Glenn Resch spit the bit in a forgettable Game 6 loss in Toronto, then he allowed Lanny McDonald to chip in the overtime winner on Long Island one game later.

11. 1982 Montreal Canadiens

Montreal Canadiens center Doug Wickenheiser

Record (league rank): 46-17-17 (3rd of 21)

Goals differential (league rank): +137 (1st)

SRS (league rank): 1.68 (1st)

Head coach: Bob Berry

Fab five: Goalie Rick Wamsley, defensemen Brian Engblom, Rod Langway and Larry Robinson, forward Keith Acton

Where they failed: Lost to Quebec Nordiques (3-2) in Adams Division semifinals

Bottom line: The Habs were 27 points better in the regular season, but the records meant squat when these blood rivals slugged it out.

Dale Hunter decided the Battle of Quebec in the first minute of overtime. Or Dale "The Nuisance"' Hunter, as he was known on the ice in the "City of Saints."

The Nordiques won three games by a single goal.

10. 1976 Philadelphia Flyers

Philadelphia Flyers goalie and team captain Bobby Clarke

Record (league rank): 51-13-16 (2nd of 16)

Goals differential (league rank): +139 (2nd)

SRS (league rank): 1.62 (2nd)

Head coach: Fred Shero

Fab five: Goalie Wayne Stephenson, defenseman Jimmy Watson, forwards Bill Barber, Bobby Clarke and Reggie Leach

Where they failed: Lost to Montreal Canadiens (4-0) in Stanley Cup Final

Bottom line: Even without Bernie Parent for most of the season, metrics say this was the best team in franchise history.

Yet while his presence likely would have prevented a sweep in the final round, it’s a stretch to say the Flyboys would have three-peated against a loaded Canadiens team that would go on to raise four consecutive Stanley Cups itself.

9. 1993 Pittsburgh Penguins

Pittsburgh Penguins center Mario Lemieux

Record (league rank): 56-21-7 (1st of 24)

Goals differential (league rank): +99 (1st)

SRS (league rank): 1.23 (1st)

Head coach: Scotty Bowman

Fab five: Goalie Tom Barrasso, defenseman Larry Murphy, forwards Jaromir Jagr, Mario Lemieux and Kevin Stevens.

Where they failed: Lost to New York Islanders (4-3) in Patrick Division finals

Bottom line: If ever a team was primed for a three-peat, this was it. In a six-week stretch late in the season, "Super" Mario Lemieux and his Pen pals reeled off a 20-1-1 record on an insane 5.7 goals per game.

Turned out only the Penguins could beat the Penguins in the playoffs, where they allowed a spirited Islanders team to steal Game 7 in overtime.

Just don’t mention the name David Volek in Pittsburgh. (Look him up, kids.)

8. 1972 New York Rangers

Record (league rank): 48-17-13 (2nd of 14)

Goals differential (league rank): +125 (2nd)

SRS (league rank): 1.49 (2nd)

Head coach: Emile Francis

Fab five: Goalie Ed Giacomin, defenseman Brad Park, forwards Rod Gilbert, Vic Hadfield and Jean Ratelle

Where they failed: Lost to Boston Bruins (4-2) in Stanley Cup Final

Bottom line: In almost any other season, coach Emile Francis’ team would have broken the 1940 hex.

But the Blueshirts were stuck with a ridiculous path to the final round, as they had to go through the Montreal Canadiens (108 points) and Chicago Blackhawks (107 points) to get there.

This team had the GAG (Goal A Game) line plus a solid defensive corps and goalie tandem, but it didn’t have the great Bobby Orr, who was the difference in the final round.

7. 1974 Boston Bruins

Boston Bruins goalie Gil Gilbert and defenseman Al Sims

Record (league rank): 52-17-9 (1st of 16)

Goals differential (league rank): +128 (1st)

SRS (league rank): 1.55 (1st)

Head coach: Bep Guidolin

Fab five: Goalie Gilles Gilbert, defensemen Bobby Orr and Carol Vadnais, forwards Phil Esposito and Ken Hodge

Where they failed: Lost to New York Islanders (4-2) in league semifinals

Bottom line: This was pretty much the same nucleus whose Game 2 meltdown cost them a Stanley Cup only three years earlier. Well, they did it again. The upstart Flyers scored in the final minute of an eventual 3-2 overtime win that turned the series around.

Think the B’s would have won this thing had cheapskate management not allowed franchise goalie Gerry Cheevers to jump leagues two years earlier? Uh, us, too.

6. 1930 Boston Bruins

Record (league rank): 38-5-1 (1st of 10)

Goals differential (league rank): +81 (1st)

SRS (league rank): 1.60 (1st)

Head coach: Art Ross

Fab five: Goalie Tony Thompson, defenseman Eddie Shore, forwards Dit Clapper, Dutch Gainor and Cooney Weiland

Where they failed: Lost to Montreal Canadiens (2-0) in Stanley Cup Final

Bottom line: The class of the league didn’t lose as many as two consecutive games in the regular season.

Then the Habs wrecked their Stanley Cup repeat bid in no time as part of a bizarre best-of-three format.

Rest of the story: The league wisely expanded the series to a best-of-five shortly afterward.

5. 1975 Montreal Canadiens

Montreal Canadiens left wing Yvon Lambert and goalie Ken Dryden

Record (league rank): 47-14-9 (1st of 18)

Goals differential (league rank): +149 (1st)

SRS (league rank): 1.72 (1st)

Head coach: Scotty Bowman

Fab five: Goalie Ken Dryden, defensemen Guy Lapointe, Larry Robinson and Serge Savard, forward Guy Lafleur

Where they failed: Lost to Buffalo Sabres (4-2) in semifinals

Bottom line: Scotty Bowman’s clubs hoisted four consecutive Stanley Cups in the 1976-1979 seasons, but we tend to forget there could have been a fifth one.

The Canadiens had a 29-21 edge in goals in the semis but lost three one-goal games, two of them in overtime.

The best would be soon to come.

4. 1979 New York Islanders

Record (league rank): 51-15-14 (1st of 17)

Goals differential (league rank): +144 (1st)

SRS (league rank): 1.76 (1st)

Head coach: Al Arbour

Fab five: Goalie Glenn Resch, defenseman Denis Potvin, forwards Mike Bossy, Clark Gillies and Bryan Trottier

Where they failed: Lost to New York Rangers (4-2) in Campbell Conference semifinals

Bottom line: After the latest postseason failure, this one to their local rivals, the Isles were cast as chokers and worse.

If not for some misguided loyalty on the part of Al Arbour in goal — Glenn Resch lost all three of his starts while future Hall of Famer Billy Smith watched on the bench — they probably would have won this series and maybe one more.

Four Stanley Cups later, this bitter disappointment would be remembered as a lesson learned.

3. 1996 Detroit Red Wings

Detroit Red Wings winger Bob Errey and defensemen Viacheslav Fetisov and Vladimir Konstantinov

Record (league rank): 62-13-7 (1st of 26)

Goals differential (league rank): +144 (1st)

SRS (league rank): 1.64 (1st)

Head coach: Scotty Bowman

Fab five: Goalie Chris Osgood, defensemen Vladimir Konstantinov and Nicklas Lidstrom, forwards Sergei Federov and Steve Yzerman

Where they failed: Lost to Colorado Avalanche (4-2) in Western Conference finals

Bottom line: It took a miraculous Stevie Yzerman goal in Game 7 to get past the St. Louis Blues in the semis, but the struggles proved to be more real than imagined.

Veteran Patrick Roy outplayed the 23-year-old Chris Osgood in the next round, and what had the potential to be an epic Red Wings team became known as a historic underachiever instead.

2. 1945 Montreal Canadiens

Record (league rank): 38-8-4 (first of six)

Goals differential (league rank): plus 107 (first)

SRS (league rank): 1.78 (first)

Head coach: Dick Irvin

Fab five: Goalie Bill Durnan, defenseman Butch Bouchard, forwards Toe Blake, Elmer Lach and Maurice Richard

Where they failed: Lost to Toronto Maple Leafs (4-2) in league semifinals

Bottom line: It appeared that only one team had even the slightest chance to knock off the mighty Habs in the playoffs.

That would be the third-place Maple Leafs, who got the best of them in the regular-season series, 5-4-1, the only opponent to do so.

When the Canadian rivals beat them four more times in the postseason, all by a mere goal, the outcome was hardly a fluke.

1. 1971 Boston Bruins

Record (league rank): 57-14-7 (1st of 14)

Goals differential (league rank): +192 (1st)

SRS (league rank): 2.29 (1st)

Head coach: Tom Johnson

Fab Five: Goalie Gerry Cheevers, defenseman Bobby Orr, forwards John Bucyk, Phil Esposito and Ken Hodge

Where they failed: Lost to Montreal Canadiens (4-3) in Eastern Conference quarterfinals

Bottom line: Don’t waste your breath on arguments here. The Big, Bad Bruins averaged 5.1 goals per game in the regular season and broke all kinds of league records. The dunderheaded decision to start 35-year-old backup Eddie Johnston in the pivotal Game 2 set the upset in motion.

The Habs scored the last five goals in a 7-5 shocker that gave them new life. Then, a rookie netminder named Ken Dryden waved his magic stick the rest of the way.

Want to get a dirty look from a New England sports fan? Just mention the 1971 Bruins.