So, the Washington Capitals are Presidents Trophy winners for the second year in a row and third time in the last eight seasons.

That and a quarter will buy them a cup of coffee. Which is pretty much what they’ve had in the past 10 post-seasons, despite being a perennial powerhouse boasting the league’s biggest sniper in Alex Ovechkin.

The Caps haven’t been past the second round of the playoffs since OV arrived in 2005-06 and the clock continues to tick. Now, there is no reason to entertain the wild thought that the youthful and inexperienced Toronto Maple Leafs could pull off a first round shocker against the Capitals. Or, is there? Wait and see.

Since expansion and beyond, there have been quite a regular season Goliaths sent to undignified defeat by relative Davids. And that is what makes playoff hockey — so much different than its regular season counterpart — so exciting and unpredictable.

Here are 10 embarrassing defeats suffered by NHL front-runners in the first round of the playoffs (in chronological order with seed in brackets).

10. Edmonton Oilers (14) Defeat Montreal Canadiens (3) – 1981

In 1981, the NHL didn’t have the complicated — and sometimes unfair — system it does now. The league had 20 teams, with 16 making the playoffs. And those 16 teams were ranked 1-16, with the no. 1 seed playing no. 16 and down the list. That season, the upstart Edmonton Oilers, led by regular season scoring champ Wayne Gretzky, finished 14th with just 74 points in 80 games. The mighty Habs, just two years removed from a winning the fourth of four straight Stanley Cups, waltzed into the post-season with the third best record in the league and 103 points. On paper, it was a mis-match, as Montreal still had a slew of holdovers from the dynasty years, including Guy Lafleur, Larry Robinson and Steve Shutt. Well, things did not go the way the Canadiens planned at all as the high-flying Oilers swept Montreal in three straight games, by a combined score of 15-6. Gretzky, then all of 20, scored three goal and seven assists in those three games.

(AP Photo)

9. Los Angeles Kings (8) Beat Edmonton Oilers (1) – 1982

One year after sending the Montreal Canadiens packing in the first round of the playoffs, the Edmonton Oilers found themselves as the no. 1 seed in the newly formed Smythe Division of the Clarence Campbell Conference. They earned 111 points to be Campbell champs, while fellow Smythe rivals, the Los Angeles Kings limped into the playoffs with 63 points (worst among all playoff teams) as the fourth seed in the Smythe. Just like the mighty Canadiens team the Oilers vanquished in 1981, Edmonton was a star-studded squad on the way up. The Kings, on the other hand, had one good line — the Triple Crown — that consisted of Marcel Dionne, Dave Taylor and Charlie Simmer and that was about it. But, someone forgot to tell the Kings they were the underdogs. They pasted the mighty Oilers 10-8 in the first game, lost 3-2 in OT in game 2, then forced the Oilers to the wall with a 6-5 OT thriller (they came back from 5-0) dubbed “the Miracle On Manchester” in game 3. The Oilers tied it all up with a narrow 3-2 victory in game 4, forcing a game 5 back in Edmonton. The Kings and the Triple Crown line put the pedal to the metal in game 5 to win it, 7-4.

Source: nhl.com

8. San Jose Sharks (8) Clip Detroit Red Wings (1) – 1994

The San Jose Sharks, for the first two years of their existence, were a deplorable hockey club. In 164 games over two seasons (1991-92 and 1992-93) they won all of 28 and tied seven, finishing dead last in the old Smythe Division both times. In 1993-94, the improving Sharks finished eighth in the Western Conference with 82 points, a full 18 points behind no. 1 seed Detroit. This was a powerful Red Wings team on the rise that sported Sergei Fedorov, Paul Coffey, Nicklas Lidstrom, Chris Osgood and Steve Yzerman. The Sharks had a fairly no-name bunch fronted by leading scorer Sergei Makarov, who was an old man at 35 then. The Wings and Sharks traded close victories in a series many expected the Wings to sweep, except the Sharks took a 3-2 lead into game 6 at the Joe. The Wings, behind a two-goal, three-point effort from Dino Ciccarelli, whipped the Sharks 7-1 and put to bed any notion the Sharks would win the series. Only the Sharks had other ideas, winning a thrilling game 7 on a goal from little known journeyman forward Jamie Baker in the dying minutes of the third period.

Source: Greatest Hockey Legends

7. Ottawa Senators (8) Down New Jersey Devils (1) – 1998

After winning their first Stanley Cup in 1995, the New Jersey Devils announced loudly to the NHL that they had arrived after years of playoff futility. They didn’t follow it up with success, missing the playoffs in 1996. They would come back to play two rounds in 1997 after a 104 point season and in 1997-98 they topped the Eastern Conference with 107 points, setting up a date with eighth place Ottawa in the first round. The Devils were loaded with talent that year, including future Hall of Famers Doug Gilmour, Scott Niedermayer, Scott Stevens and of course Martin Brodeur. The Senators, on the other hand, were a few years removed from being a horrible expansion club and had youngsters Alexei Yashin and Daniel Alfredsson coming into their own. The Senators would get three goals apiece from this dynamic duo, as well as hot goaltending from Damian Rhodes to stun the Devils in six games.

Mandatory Credit: Ezra C. Shaw /Allsport

6. Toronto Maple Leafs (7) Beat Ottawa Senators (2) – 2001

At the turn of the century, the Toronto Maple Leafs disposed of the Ottawa Senators in the first round of the 2000 playoffs, the beginning of a heated “Battle of Ontario” playoff rivalry. A year later, the Senators finished first in the old Northeast Division with 109 points, 19 points ahead of the hated Leafs, who finished seventh and earned another crack at the Sens in the post-season. In the lead up to the re-match, Ottawa owned the Leafs in the regular season, winning all five contests and adding fuel to a growing hockey fire. Unfortunately for the Senators, the Leafs had a rejuvenated Curtis Joseph in goal and fired up captain Mats Sundin leading the charge. Joseph would shut the Sens out in the first two games in Ottawa, while Sundin scored the winner in Game 1 and his robust winger Gary Roberts would pot two in the 3-0 Game 2 victory. The Senators would finally beat Cujo four minutes into Game 3, but it was too little too late as they scored just three goals in the series and lost in four straight.

(CP PHOTO/Kevin Frayer)

5. Might Ducks of Anaheim (7) Upset Detroit Red Wings (2) – 2003

The Stanley Cup hangover is a thing and in 2003, the Detroit Red Wings suffered a bad case of it. And the purveyor of the ugly medicine they received in the playoffs was Mighty Ducks goaltender Jean-Sebastien Giguere. That season, Mighty Ducks rookie head coach Mike Babcock steered the team to a seventh place finish in the Pacific Division, 15 points behind Central Division champion and defending Cup winners Detroit. The mighty Wings boasted scoring galore in the guise of Sergei Fedorov, Brett Hull, Brendan Shanahan, Nicklas Lidstrom, Luc Robitaille and Steve Yzerman, future Hall of Famers all. The Ducks countered with a no-name cast featuring Paul Kariya, Adam Oates and Giguere. In that fateful first round, the Ducks scored by committee and got all-world netminding from Giguere in an improbable sweep of the defending champs. Giguere, who would go on to win the Conn Smythe (even though the Ducks lost in the finals) stopped an incredible 63 of 64 shots in a 2-1 triple overtime victory in Game 1 and would allow just six goals all series to stymie the powerhouse Winged Wheels.

(CP PICTURE ARCHIVE/AP/Kevork Djansezian)

4. Edmonton Oilers (8) Defeat Detroit Red Wings (1) – 2006

The season-killing lockout of 2004-05 seemed to have been the tonic for the Edmonton Oilers franchise, who missed the playoffs twice in three seasons previous to the labor stoppage. They posted a 95-point season and squeaked into the playoffs, where they would have the daunting task of facing the President’s Trophy winning Wings, who had a lofty 124 points on 58 wins (their greatest regular season ever). The Wings, however, would suffer the indignity of being taken out by a relative lightweight in the first round for the second time in three post-seasons. This time around, though, they weren’t undone by a goaltender — Edmonton’s Dwayne Roloson did have a hand in it — but by a rare playoff one-hit wonder by the name of Fernando Pisani. The Edmonton native, who had all of one goal in six playoff games before that 2006 series and 18 goals in 80 games during the regular season, lit up Detroit for five goals in the Oilers 4-2 series win. His two markers in Game 6 were pivotal in Edmonton disposing of Detroit. He fired a league high 14 in total as the Oilers went all the way to the finals.

(AP Photo/Paul Sancya)

3. Anaheim Ducks (8) Upend San Jose Sharks (1) – 2009

For the last 15 years or so, the San Jose Sharks have been the perennial bridesmaids in the post-season. They have teased their fans with outstanding regular season play, only to fall horribly short in the playoffs. No Big Dance defeat, however, stung worse than the six-game loss to the Anaheim Ducks in 2009. The Sharks, led by Jumbo Joe Thornton and Patrick Marleau, had their best season ever, winning 53 games and the President’s Trophy with 117 points. Facing them would be the Ducks, who limped into eighth place in the West with 91 points, just two years after winning their first Stanley Cup. The Ducks, again, would get outstanding goaltending to stun a superior foe, this time by Jonas Hiller, who was in just his second season and split duties with 2003 playoff hero Jean-Sebastien Giguere. Hiller posted two shutouts against the high-flying Sharks, including a 35-save effort in Game 1 (2-0) and another 31-save performance in Game 4 (4-0).

(AP Photo/Mark Avery)

2. Montreal Canadiens (8) Shock Washington Capitals (1) – 2010

The Sharks are not alone in knowing playoff sorrow after regular season triumph. Just ask the Washington Capitals, who won two Presidents trophies in seven seasons (they added a third this year) but failed to advance past the second round of the playoffs. In 2009-10, the Caps, who got another 50-goal season from sniper Alex Ovechkin, blew away the competition with their best season ever, winning 54 games and recording 121 points. The Habs were nobody’s favorite going into a first round set with the Capitals, as they accumulated just 88 points and were the eighth seed. To boot, Montreal scored by committee and got adequate goaltending from Jaroslav Halak and a young Carey Price. And it would be Halak, not Price, who would be the stone wall the Caps superb offence could barely penetrate. In a thrilling seven-game series, Halak would stop 94 of 96 shots in Games 6 and 7 (4-1 and 2-1 wins) as Montreal came back from a 3-1 series deficit to send Washington packing.

(AP Photo/Nick Wass)

1. Los Angeles Kings (8) Stun Vancouver Canucks (1) – 2012

There would be no solace in defeat for the Presidents trophy winning Vancouver Canucks in 2012, even though they lost to the eventual champion Los Angeles Kings in the first round. Much was expected of the Canucks that year, as they came within a win of capturing their first championship against Boston in 2011 (after winning the first of back-to-back President’s trophies no less). They had 111 points, which were 16 better than eighth place L.A. The two teams entered the playoffs having split their season series 2-2 and on paper, even though the Canucks finished way ahead, there weren’t many discernible differences. And in the series, goaltending, or lack thereof, and timely scoring would be the difference. The Kings’ Jonathan Quick helped steal the series, stopping 46 of 48 shots in Game 2, where the Kings also got two goals from Dustin Brown to win 4-2. Quick then stopped all 41 shots he faced in Game 3 to put the Kings up 3-0 on the way to the five-game upset.

THE CANADIAN PRESS/Darryl Dyck