The Isles had the most points in the league with 116 and a winning percentage of .725 while the Rangers, although fifth overall in the league had 25 points less with 91. Led by a rejuvinated Phil Esposito, Don Maloney and goaltender John Davidson, the Blueshirts beat the Isles four games to two. The Islanders only two wins came in overtime. In my opinion, the fact that this upset was so late in the playoffs and not in the first round adds to it's lustre.
9. 1994-95 First Round, New York Rangers defeat Quebec Nordiques
The fourteenth overall Rangers knocked off the second place Nordiques in their swan song in La Belle Provence. With 65 points in 48 games for a .677 Win Pct, the Nordiques were on their way to winning the Cup next year, in Colorado but were beaten by the sub.500 Rangers. New York's 47 points translates to 8o in an 82 game season, while Quebec's would have been 111 points.
8. 1992-93 Second Round, New York Islanders defeat Pittsburgh Penguins
31 points seperated 13th ranked New York from the first overall Penguins, yet Islanders David Volek potted the winner in game seven overtime to knock out the defending champs.
7. 2008-09 First Round, Anaheim defeats San Jose
This one saw the 18th place Ducks knock out the President Trophy winning Sharks. San Jose had 117 points to Anaheim's 91 for a difference of 26 points. The differential of 18 spots in regular season ranking is second only to this year's Montreal/Washington.
6. 1950-51 Semi-Finals, Montreal defeats Detroit
Montreal with 65 points in 70 games knocked off the Wings who tallied 101 points in the season. Projected to 82 games Detroit 118 points, Montreal 76. This difference of 42 points by an upsetting team would be the fourth most ever.
5a. 1990-91 First Round, Minnesota defeats Chicago
5b.1990-91 Second Round, Minnesota defeats St.Louis
The sixteenth place North Stars pulled off back-to-back amazing upsets on the way to the Stanley Cup finals. The 68 point Stars first beat the top seed Blackhawks who had 106 points in six games, then they did the same to the second overall, 105 point Blues. Their run continued past the Oilers in the Semi-finals who were on an upset binge of their own. The Oilers with 80 points had beaten 102 point Calgary and 100 point Los Angeles before losing in five to the upstart North Stars.
4. 1929-30 Stanley Cup Finals, Montreal defeats Boston
The only reason this one isn't the greatest upset of all-time is because the final series consisted of only two games. The Bruins had complied 77 points in 44 games for a Win Pct of .875, the highest in NHL history. The Canadiens .580 Pct translates to 95 today, yet Boston's projects to 142. This 47 point difference would rank second all-time.
3. 1944-45 Semi-Finals, Toronto defeats Montreal
The Leafs were two points over .500, yet knocked off Montreal who had a Pct of .800. This translates to 85 pts for Toronto, 131 for Montreal and a pro-rated difference of 46 points. Led by 19 year old 'Teeder' Kennedy and Frank 'Ulcers' McCool in net, the Leafs won in six games. They managed to endure a 10-3 loss to the Habs in game five before finishing them off.
2. 2009-10 First Round, Montreal defeats Washington
Although finishing 8th in the East, the Canadiens were actually the 20th best team in the regular season due to the strength of the Western Conference. The twenty spots seperating the teams is the most ever for an upsetting team.
1. 1981-82 First Round, Los Angeles defeats Edmonton
This one has it all, a 17th ranked team defeating a second overall. A 63 point team defeating a 111 point squad. Daryl Evans (pictured at top) defeating Wayne Gretzky. The 48 point differential is the most ever. Although this was only a best of five series, it has to rank as the greatest upset in NHL history.
1937-38 Finals, Chicago defeats Toronto
This one saw the worst ever Stanley Cup winning team in Chicago which finished the regular season with a .385 Win Pct. They beat Toronto 3 games to 1 and went 8-2 overall in the playoffs after winning only 14 in 48 games all season.
1970-71 First Round, Montreal defeats Boston
Although Boston had 121 points, Montreal's 97 was nothing to sneeze at, and the Habs actually were fouth overall in the league. This one is an over-rated upset in my mind.
1985-86 First Round, Toronto defeats Chicago
Anytime a team with a .356 winning Pct and 57 points beats an 86 point team, it is a huge upset.