March 24, 1936: 116:30 of overtime
Detroit Red Wings 1 - Montreal Maroons 0
Mud Bruneteau's goal in the 6th overtime period gives the Red Wings the first game in a best-of-five semifinal. Detroit goes on to win the Stanley Cup.
April 3, 1933: 104:46 of overtime
Toronto Maple Leafs 1 - Boston Bruins 0
Another six-overtime marathon. Ken Doraty scores to clinch the deciding game of a best-of-five semifinal. Toronto will ose to the New York Rangers in the Stanley Cup Final.
May 4, 2000: 92:01 of overtime
Philadelphia Flyers 2 - Pittsburgh Penguins 1
In the 5th overtime period, Keith Primeau's goal ties the second-round series at two games apiece. The Flyers win the next two games, but blow a 3-1 series lead to New Jersey and lose the Eastern Conference Final.
April 24, 2003: 80:48 of overtime
Anaheim Ducks 4 - Dallas Stars 3
Petr Sykora scores less than a minute into the 5th overtime period, and the Ducks win Game One of the second round series. Anaheim goes all the way to the Stanley Cup Final before losing to New Jersey.
April 24, 1996: 79:15
Pittsburgh Penguins 3 - Washington Capitals 2
Petr Nedved's goal in the 4th overtime ties the opening round series at two games each. Pittsburgh will win the series and eventually lose to Florida in the Eastern Conference Final.
April 11, 2007: 78:06
Vancouver Canucks 5 - Dallas Stars 4
The Canucks open the playoffs with a win, courtesy of Henrik Sedin's goal in the 4th overtime period. Vancouver will prevail in a seven-game series, and be eliminated in the second round by the eventual champions from Anaheim.
March 23, 1943: 70:18
Toronto Maple Leafs 3 - Detroit Red Wings 2
Jack McLean scores for the Leafs in the 4th overtime, tying the semifinal series at one game apiece. But Detroit goes on to win the series and the Stanley Cup.
May 4, 2008: 69:03
Dallas Stars 2 - San Jose Sharks 1
In the 4th overtime period, Brenden Morrow's clinches game six for the Stars, eliminating San Jose and sending Dallas to the Western Conference Final.
March 28, 1930: 68:52
Montreal Canadiens 2 - New York Rangers 1
A goal by Gus Rivers in the 4th OT gives Montreal the first game in a best-of-three semifinal. The Canadiens sweep the Rangers and then the Bruins to win the Stanley Cup.
April 18, 1987: 68:47
New York Islanders 3 - Washington Capitals 2
Game seven of the opening round series goes to four overtime periods before Pat LaFontaine wins it for the Islanders. They'll lose to Philadelphia in seven games in round two.