Sometimes the hardest step on the road to the Stanley Cup is the first one. Just ask the Washington Capitals.

Last season's Caps became the latest victims of the upset jinx that has bitten many a regular-season powerhouse. Washington rolled to the first Presidents' Trophy in franchise history by piling up 121 points, but they couldn't get past the eighth-place Montreal Canadiens, who had finished with 33 fewer points than the Caps in the regular season.

The inability to get past the first round of the playoffs has sent more than one Cup favorite home early. No matter how great a team's regular season is, all those points mean nothing once the playoffs start -- especially against an opponent that often sees a first-round upset as the way to atone for a disappointing season.

Here's a look at some of the biggest first-round upsets in playoff history since expansion enlarged the playoffs to more than two rounds:

1982: Los Angeles vs. Edmonton

Nearly three decades later, this remains the gold standard of upsets.

Someone forgot to tell the Kings they were supposed to roll over for the most prolific offensive team in NHL history. The Oilers had pulverized the Smythe Division during the regular season, piling up goals at a historic rate -- Wayne Gretzky alone accounted for 92 -- while piling up 111 points. The fourth-place Kings had just 63, a drop of 36 from 1980-81.

Then again, maybe the 48-point disparity in the standings made the Oilers a little too comfortable. The Kings shocked the opening-night crowd at Northlands Coliseum with a 10-8 victory. They nearly won Game 2 before Gretzky's goal at 6:20 of overtime evened the series.

But it was Game 3 -- forever known in Los Angeles as the "Miracle on Manchester" -- that made this series one for the history books.

The Oilers were at their dynamic best through the first two periods at the Forum on April 10 -- they led 5-0 and were embarrassing the Kings in their own building. But defenseman Jay Wells scored with 17:14 left in the third period, and the Kings got a spark of life. Goals by Doug Smith and Charlie Simmer cut the Oilers' lead to 5-3 with five minutes left.

Edmonton's Garry Unger then took a five-minute major for high-sticking Kings defenseman Dave Lewis, who was assessed a minor for roughing. During the 4-on-4, Edmonton's Pat Hughes had a clean breakaway, only to be stopped by goalie Mario Lessard. Shortly afterward, defenseman Mark Hardy found himself alone in the slot and beat Grant Fuhr with a wrist shot. The margin was one, and the Forum was rocking.

With less than 90 seconds left, Hughes again found himself alone on a shorthanded breakaway, but Lessard stopped him for a second time. The Kings then worked the puck into the Oilers' zone, pulled Lessard, and with the clock ticking down, Hardy got the puck in the high slot and fired a shot at Fuhr. The goaltender got a pad on the puck but couldn't control the rebound. Rookie Steve Bozek's backhander hit the back of the net with five seconds remaining, forcing overtime as bedlam took over the Forum.

The Kings didn't need long to complete the greatest comeback in playoff history. Smith won a draw in the Oilers' zone and rookie Daryl Evans scored right off the faceoff at 2:35, moving the Kings within one victory of the NHL's biggest upset.

"I wasn't really picking any opening," Evans said. "I just was trying to get the shot on net. As it turned out I beat Fuhr up high over his right shoulder -- and before I knew it everyone on the team was piling on top of me at the other end of the ice."

The Oilers rebounded with a 3-2 win in Game 4, sending the series back to Edmonton for what their fans were sure would be a series-clinching victory. Instead, the nothing-to-lose Kings jumped to a 2-0 lead and rolled to a 7-4 victory as Evans scored 2 goals. The 48-point disparity remains the largest disparity ever overcome by a series winner.

The Kings were ousted in the second round by Vancouver, while the Oilers regrouped and made the Stanley Cup Final in 1983, where they lost to the New York Islanders. A year later, they beat the Islanders for the first of their five titles in seven years.

1971: Montreal vs. Boston

In one regard, the Bruins were the Oilers of their day -- a team that scored more than anyone thought possible. But unlike the Oilers' kiddie corps, the Bruins were the defending Stanley Cup champions -- and they had muscle to go with all that firepower. "The Big Bad Bruins" had set an NHL record by winning their last 10 playoff games in 1970 on the way to their first Cup since 1939.

The 1970-71 Bruins were an offensive machine the likes of which the NHL had never seen: Phil Esposito set NHL records with 76 goals and 152 points, Bobby Orr piled up an NHL-record 102 assists and Boston ran away with the Eastern Division title, piling up 121 points while outscoring their opponents by a then-record 192 goals. Under the format in use at the time, that earned them a first-round meeting with third-place Montreal, which was coming off its first non-playoff season since 1948 and had finished 24 points behind the Bruins.

Not only were the Canadiens decided underdogs, they were going to be using an untested goaltender. On the day before the series began, GM Sam Pollock stunned his team and all of Montreal when he announced that Ken Dryden, a 23-year-old rookie who had played only six NHL games (winning them all) in the final weeks of the season, would be the Habs' starter for the playoffs.

Dryden didn't get off to an auspicious beginning. The Bruins beat the Canadiens 3-1 in the opener and took a 5-1 lead midway through the second period in Game 2 -- only to see the Canadiens score six unanswered goals, five in the third period, for a 7-5 victory. Henri Richard started the comeback with an unassisted goal at 15:33 of the second, and Jean Beliveau scored twice in the third.

Montreal won Game 3 at the Forum 3-1, but the Bruins evened the series with a 5-2 win in Montreal and took a 3-2 series lead with a 7-3 rout at Boston Garden. However, the Canadiens and their rookie goalie weren't done -- Richard scored twice in Montreal's 8-3 victory in Game 6, sending the series back to Boston for the deciding game.

Ken Hodge put the Bruins ahead at 6:50, but Frank Mahovlich and Rejean Houle scored before the end of the period to put Montreal in front to stay. J.C. Tremblay made it 3-1 late in the second period and Mahovlich scored again 14 seconds into the third period.

Meanwhile, the Bruins couldn't do anything against Dryden, who stopped 13 shots in the first period and all 16 he faced in the second. Johnny Bucyk finally cut the margin to 4-2 just 62 seconds into the third, but Dryden stymied the Bruins the rest of the way. At one point, Esposito was so frustrated after being robbed by the 6-foot-4 rookie that he swung his stick into the glass. Espo had 11 shots on goal and couldn't beat Dryden once.

"Words cannot even begin to describe the way Dryden played," Hodge told reporters after Dryden finished with 46 saves as the Canadiens beat the Bruins in a playoff series for the 11th straight time. They went on to beat Minnesota and Chicago for the Stanley Cup. The Bruins rebounded to win the Cup the following year -- but haven't won since.

2010: Montreal vs. Washington

The 2009-10 Capitals were (and still are) the best offensive team of the 21st century. They piled up goals at a rate unseen in a decade and a half. Alex Ovechkin reached the 50-goal mark for the fourth time in his five NHL seasons, and linemate Nicklas Backstrom joined Ovechkin as half of the NHL's 100-point club. They packed arenas around the League while finishing first in the regular-season standings.

No one expected Montreal to give the Caps much of a test in their first-round matchup. The Canadiens were the final qualifier in the Eastern Conference with just 88 points, the fewest of any playoff team since the introduction of the shootout in 2005.

But the Canadiens had a secret weapon: goaltender Jaroslav Halak, who had played his way past Carey Price and into the starting job, and stymied the Caps in the opening game, stopping 45 of 47 shots before Tomas Plekanec's goal at 13:19 of overtime gave Montreal a 3-2 victory.

The Caps shook off the Game 1 loss by winning 6-5 in overtime in Game 2 to square the series, then trampled the Canadiens 5-1 and 6-3 at home to take a 3-1 lead in the best-of-7 series. The wins at Montreal had been so easy that Caps coach Bruce Boudreau spent part of his post-game press conference following Game 4 warning that the series wasn't over yet.

How right he was.

With the full house at Washington's Verizon Center ready to celebrate, Halak -- who was lifted in Game 3 and benched in Game 4 -- stopped 37 of 38 shots as Montreal won 2-1, making a pair of first-period goals stand up.

But that was just a warm-up act. Three days later, Halak stopped 53 of 54 shots as Montreal won 4-1.

"I think we played great and we just didn't score," said a still confident but definitely stunned Ovechkin. "It's only one guy. They just score goals and go back and leave all the pressure for their goalie. He (did) an unbelievable job. What more can you say?"

The Caps had one more chance in Game 7, but once again Halak was too much. He stopped 41 shots, allowing only a late goal by Brooks Laich, to send the Caps home for the summer as Montreal won 2-1.

"After we were trailing 3-1, I said to myself, 'We've got nothing to lose. Just try to do your best and have fun,'" Halak said of his remarkable turnaround, which saw him stop 131 of 134 shots in the final three games.

If there was any consolation for the Caps, Halak did the same thing to their biggest rivals in the next round, upsetting Sidney Crosby and the Pittsburgh Penguins before losing to Philadelphia in the Eastern Conference Finals.

1994: San Jose vs. Detroit

The Detroit Red Wings were the best in the West in 1994; in fact, they were the only team in the conference to reach the 100-point mark -- and were looking to end a Cup drought that reached back to 1955.

They certainly weren't expecting a first-round challenge from the San Jose Sharks, a third-year franchise making its first playoff appearance. Though San Jose made the playoffs thanks to an NHL-record 58 point improvement, the Sharks were the only club in the 16-team field that came in with a losing record. The question for most fans in both cities was whether San Jose even would win a game.

The answer came quickly -- the Sharks stunned a sellout crowd at Joe Louis Arena with a 5-4 victory in the opener. Vlastimil Kroupa, a teenager, scored the game-winner when he beat Bob Essensa under his glove with 4:24 left in regulation.

The Wings changed goaltenders in Game 2, and 21-year-old rookie Chris Osgood coasted to a 4-0 victory. Detroit then spoiled the first home playoff game in Sharks history with a 3-2 win.

But the Sharks rallied behind goaltender Arturs Irbe, winning the next two games, 4-3 and 6-4 at home, to take a 3-2 series lead back to Detroit (the series was played with a 2-3-2 format). The Wings calmed their nervous fans by scoring the first five goals in Game 6, routing Irbe on the way to a 7-1 victory.

However, one of the good things about young teams is that they're often too young to be scared or intimidated, and that was the case for San Jose in Game 7. Though the Wings were outplaying his team, Irbe kept the Sharks in the game through the first two-plus periods, and the score was tied 3-3 midway through the final period.

Osgood then made a rookie mistake, trying to fire a pass up the right side. Instead, he put the puck right on the stick of Jamie Baker, who quickly ripped a slap shot into the wide-open net with 6:35 left in regulation. Irbe made 11 saves in the final period, and the Sharks skated off with a 4-3 victory in the first playoff series in franchise history.

"If I'd made that play, we'd still be playing,” a tearful Osgood said after the game. "All I can think about is the last 10 minutes of that game."

The Sharks were bounced in the second round by Toronto, losing a seventh game at Maple Leaf Gardens. The Wings rebounded to make the Stanley Cup Final in 1995 and finally ended their championship drought two years later. They repeated in 1998 with Osgood in goal -- and he was in goal again 10 years later for another Cup with the Wings.

1991: Minnesota vs. Chicago

Rookie goaltender Ed Belfour was the toast of the Windy City in the spring of 1991 after leading the Blackhawks to an NHL-best 106-point season with 43 victories and a 2.47 goals-against average. He was so good that the Hawks had no problem trading a promising youngster named Dominik Hasek to the Buffalo Sabres.

The Hawks needed all of those 106 points to edge the St. Louis Blues for the Norris Division and Western Conference titles. That earned them a first-round meeting with the Minnesota North Stars, who managed just 68 points (although they were outscored by only 10 goals).

The 38-point disparity meant nothing in the series opener when Brian Propp scored a power-play goal 4:14 into overtime to give Minnesota a 4-3 victory. The Blackhawks regrouped to even the series with a 5-2 win in Game 2, and then appeared to take charge by rallying from a 5-2 deficit for a 6-5 win in Game 3. Minnesota scored five times in the first period, but the Hawks pulled even early in the third period on a goal by Steve Thomas, then went ahead to stay on Jeremy Roenick's goal with 13:45 remaining in regulation.

However, the North Stars pulled themselves together and evened the series with a 3-1 victory in Game 4 -- then stunned a full house at Chicago Stadium with a 6-0 victory to take a 3-2 series lead. The Hawks spent the night parading to the penalty box, and Minnesota made them pay by scoring five power-play goals.

Back at the Met Center, Brian Bellows, who had 4 assists in Game 5, scored twice and set up another goal as the Stars eliminated Chicago with a 3-1 win in Game 6.

The 38-point disparity is the second-largest overcome by any series winner. But the North Stars weren't finished -- they beat St. Louis and Edmonton to become the first team with a winning percentage under .430 to make the Stanley Cup Final since the 1938 Blackhawks. Minnesota won Games 1 and 3 against Pittsburgh, but lost the series in six games.

Chicago rebounded to make the Stanley Cup Final in 1992, but was swept by the Penguins after winning 10 straight playoff games. The Hawks finally ended a 49-year Cup drought last spring, beating Philadelphia for their first championship since 1961.

2006: Edmonton vs. Detroit

Dwayne Roloson was a journeyman goalie acquired by the Edmonton Oilers in hope that he could get them to the playoffs. He did -- the Oilers qualified on the next-to-last night of the season as the eighth and final team in the Western Conference. But with 95 points, they were 29 behind the Red Wings, whose 124 points were 11 more than any other team in the League.

The Wings outshot Edmonton 57-25 in the opener, but it wasn't until Kirk Maltby's goal 2:39 into the second overtime that they skated off with a 3-2 victory. The heartbreaking loss didn't have any effect on the Oilers -- Roloson made 33 saves in Game 2, and Edmonton got goals by Brad Winchester and Fernando Pisani 57 seconds apart late in the second period for a 4-2 victory.

The Oilers came home and got a 44-save performance from Roloson and a goal by Jarret Stoll 8:44 into the second overtime for a 4-3 victory. Detroit rebounded in Game 4, scoring three power-play goals in a 4-2 victory.

But Roloson, the Oilers' best player in the first four games, rose to the occasion in Game 5, making 30 saves as the Oilers scored three second-period goals and survived a late Detroit blitz to go home with a 3-2 win.

Game 6 saw the Red Wings take a 2-0 lead after two periods, only to have Pisani score twice in the first 6:40 of the third period to tie the score. Johan Franzen scored midway through the third period to put Detroit back in front, but Ales Hemsky tied the game with a power-play goal at 16:07, then triggered one of the biggest celebrations Edmonton had seen in years when he beat Manny Legace with 1:06 left in regulation. It was the Oilers' first playoff-clinching win at home in 14 years.

"I haven't seen anything like that," said Roloson, who finished with 211 saves in the six-game series. "The place erupted. It was unbelievable."

Roloson continued his heroics by backstopping the Oilers to the Stanley Cup Final, but was injured in Game 1 and had to watch as Edmonton lost in seven games to Carolina. In 2007, Detroit was eliminated in the Western Conference Finals by Anaheim, which went on to win the Cup. The Wings were first overall in 2007-08 and went on to beat Pittsburgh in a six-game Final.

2000: San Jose vs. St. Louis

The Blues never had missed the playoffs since entering the NHL in 1967, but they never had enjoyed a season like 1999-2000, when they won the Presidents' Trophy with 114 points. That was 27 more than the Sharks, whose 87 points were the fewest among playoff qualifiers in the West and 15th in the 16-team playoff field. San Jose was 0-4-1 against the Blues during the regular season.

St. Louis won the opener 5-3, but then the puck started taking some funny bounces. The Sharks tied the series with a 4-2 win, aided by a goal scored from behind the Blues net by defenseman Bryan Marchment.

The series moved west, and the Sharks went in front with a 2-1 victory as Owen Nolan scored twice. The funny bounces continued: four of the Sharks' goals in the first three games went into the net off a St. Louis player, with one occurring when defenseman Marc Bergevin deflected the puck over the goal line with his glove while trying to knock it behind the net.

The Sharks' 3-2 win in Game 4 left them one win away from the upset, but St. Louis wouldn't go down without a fight -- they had rallied from a 3-1 deficit in 1999 to beat Phoenix in seven games.

Chris Pronger scored twice in Game 5 to lead the Blues to a 5-3 win, and Scott Young's hat trick spoiled what San Jose fans had hoped would be a clinching party in Game 6 -- the Blues scored the game's first six goals and cruised to a 6-3 win.

The Blues had home ice for Game 7, but that wasn't necessarily a good thing -- in their only two playoff series victories, the Sharks had pulled first-round upsets against Detroit in 1994 and Calgary in 1995 by winning Game 7 on the road.

Sure enough, the Sharks found a way this time, too. Ronnie Stern gave them a 1-0 lead at 2:51, and Nolan made it 2-0 with another surprising goal -- a 65-footer than fooled Roman Turek with 10 seconds left in the opening period.

"It's been a fluky series for goals," Nolan said afterwards. "I thought why not just shoot it on net and see what happens? He bobbled it and it went in."

Jeff Friesen scored in the second period, and all the Blues could manage on their 22 shots at Steve Shields was Young's power-play goal early in the third period.

"Obviously there was a lot of talk about us going a long way," Young said after the greatest season in Blues history ended prematurely. "But you can never look past the first round. It's something that we didn't seem to mentally prepare for."

The Sharks lasted only five games against Dallas in the second round. The Blues dropped off in the regular season in 2000-01, but did make it to the conference championship before losing to Colorado.

2003: Anaheim vs. Detroit

Detroit came into the 2003 playoffs primed to repeat as Stanley Cup champions. The Wings had rolled to the Central Division title with 110 points, their fourth consecutive 100-point season, and were playing an Anaheim team that hadn't made the playoffs in four years.

The seventh-seeded Mighty Ducks had lost three of their four regular-season meetings with Detroit and had been swept by the Wings in their two previous playoff meetings, but Anaheim made sure there would not be a third sweep by winning the opener 3-2 on Paul Kariya's goal 3:18 into the third overtime. The Wings got two first-period goals, but couldn't get another puck past Jean-Sebastien Giguere, who made 63 saves.

Giguere had stopped 74 consecutive shots before Jason Woolley beat him early in the second period of Game 2 to put Detroit ahead. The Wings led 2-1 after two periods and appeared to be on the way to a series-tying victory before the Ducks scored a pair of late goals to win 3-2. Jason Krog tied the game with 6:26 remaining, and Steve Thomas stunned the sellout crowd in Hockeytown when he ripped a slap shot past Curtis Joseph with 4:14 left in regulation.

The Wings still had reason to hope -- they had, after all, overcome a 2-0 deficit to beat Vancouver in the first round in 2002. But Giguere had other ideas -- he made goals by Samuel Pahlsson and Stanislav Chistov stand up by stopping 36 shots in a 2-1 win in Game 3.

Anaheim completed one of the most stunning sweeps in NHL history with a 3-2 overtime victory in Game 4. Steve Rucchin's winner at 6:53 of extra time completed the first series sweep of a defending Stanley Cup champion since 1952.

"If you would have asked me at the beginning of the series about a sweep, I would have said, 'No,'" Giguere said after stopping 32 shots in the clincher.

In his first NHL playoff series, Giguere stopped 165 of 171 shots and had a 1.24 goals-against average in the four-game sweep. He continued his brilliance by leading the Mighty Ducks all the way to the seventh game of the Stanley Cup Final before New Jersey's 3-0 victory denied them what would have been one of the most improbable championships ever. Though his team didn't win, Giguere was awarded the Conn Smythe Trophy as playoff MVP.

1998: Ottawa vs. New Jersey

The Ottawa Senators had made the playoffs for the first time in 1997, but they did it despite finishing with a sub-.500 record. Not until 1997-98, their sixth season in the NHL, did the Senators finish with more wins than losses. But their team-record 83 points only was good enough for eighth place, earning the Senators a first-round matchup against the Eastern Conference-champion New Jersey Devils, who piled up 107 points and still had the core of the team that had won the Stanley Cup three years earlier.

"This is the best team in the Devils' history," goaltender Martin Brodeur said before the series opened. "Everybody remembers you for playoff hockey."

However, Ottawa goaltender Damian Rhodes closed the regular season on a 5-0-2 roll, and he stayed hot in Game 1, stopping 28 shots and outdueling Brodeur as the Senators stunned the Devils by winning 2-1 on a goal by Bruce Gardiner 5:58 into overtime.

The Devils rebounded with a 3-1 win in Game 2, but the series moved to Ottawa, where the Senators got another brilliant effort from Rhodes in Game 3. He outplayed Brodeur again, stopping 30 shots before Alexei Yashin scored the winner 2:47 into overtime for another 2-1 victory.

"I got a good piece of it," Yashin said. "I didn't see it; I just saw the fans' reaction. I knew it was pretty good."

The Senators came out flying in Game 4, with Daniel Alfredsson scoring three times to help Ottawa grab a 4-1 lead. As often happens with young teams, however, holding the lead was tougher than getting it -- Scott Stevens and Doug Gilmour each scored to make it a one-goal game, but Rhodes made a game-saving stop on Gilmour in the final minute to preserve the 4-3 victory.

"I don't know if it was the best night of my career," Alfredsson said, "but it was the most fun. I was satisfied with my play in the first three games. I thought if I stuck with it something good would happen. But I wasn't expecting three goals."

The Devils won Game 5, beating the Senators 3-1 in New Jersey. But with a chance to put the series away before a home crowd, the Senators won 4-1 to earn the first playoff series victory in franchise history.

On paper, it was a shocker. To the Senators, it was not.

"We defied the odds," Ottawa defenseman Lance Pitlick said. "They didn't give us any respect the whole series and we were the better team. They always had excuses for why we beat them, but they don't have any in the end."

To the Devils, however, it was a stunning early end to what they had hoped would be a long playoff run.

"It's devastating," defenseman Ken Daneyko said of the early exit. "Probably the most heartbroken I've ever been."

1986: New York Rangers vs. Philadelphia

The Flyers had toyed with the Rangers in the opening round of the 1985 playoffs, sweeping them on the way to the Stanley Cup Final. The Rangers had improved from 62 points in 1984-85 to 78 in 1985-86, but they still weren't expected to put up much of a fight in the best-of-five series against a Flyers team that had finished first in the East with 110 points.

But the Rangers did have goaltender John Vanbiesbrouck, who earned the Vezina Trophy for his regular-season performance and carried his excellence into the postseason. "Beezer" was brilliant in the opener, making 31 saves in a 6-2 victory that broke the Rangers' 11-game losing streak at the Spectrum. New York stood up to the Flyers' intimidation efforts and made Philadelphia pay by getting 2 power-play goals from Mike Ridley.

Vanbiesbrouck also allowed just two goals in Game 2 -- but this time, the Flyers made them stand up for a 2-1 victory.

The Rangers, the lowest-scoring team in the Eastern Conference, scored just once in the first two periods of Game 3 at Madison Square Garden, but then erupted for four goals in the final 20 minutes (three in 38 seconds) for a 5-2 victory. One night later, they had a chance to close out the Flyers in the best-of-five series but couldn't do it. Philadelphia looked every bit like the beast of the East in a 7-2 victory.

That meant the Rangers would have to win another game at the Spectrum, one of the most feared arenas in the NHL. And they did it.

Pierre Larouche, Willie Huber and Mark Osborne scored to give the Rangers a 3-1 lead after two periods. Vanbiesbrouck, who finished with 34 saves, allowed a goal midway through the final period, but kept the Flyers from tying the game until Kelly Miller and Don Maloney hit the empty net in the final minute.

It was hard to say who was more stunned by the outcome -- the Flyers fans or the Rangers themselves.

"If you told me last week we'd be here now," defenseman James Patrick told writers in the jubilant locker room, "I'd say you were crazy."

The Rangers went on to beat Washington before losing to Montreal in the Eastern Conference Finals. The Flyers got even in 1987, however, when they knocked off the Rangers in the first round on the way to another trip to the Stanley Cup Final.