5. Dallas Stars at Vancouver Canucks (April 11, 2007)
OT Length: 78:06 (Fourth Overtime)
Game and Round: Game #1, First Round (Western Conference quarterfinal)
Result: 5-4 Vancouver
Game-Winning Goal: Henrik Sedin
Vancouver fans were treated to a marathon playoff opener between the sixth-seeded Stars and third-seeded Canucks. The Stars scored two unanswered third-period goals to send Game 1 into overtime.
The Canucks, who were favored, were comprehensively outplayed, out-chanced, and outshot. The Stars peppered Roberto Luongo with 76 shots, 36 of which came in overtime. Dallas’ Marty Turco faced 56 shots in the losing effort.
With just 1:54 remaining in the fourth overtime period, Henrik Sedin scored the winner to send Canucks fans into a delirious state. During his decorated career, Sedin scored just one other overtime winner in the 2001-02 playoffs.
The Canucks won two of the three overtime encounters in the series, eventually outlasting Dallas in seven games.
4. Pittsburgh Penguins at Washington Capitals (April 24, 1996)
OT Length: 79:15 (Fourth Overtime)
Game and Round: Game #4, First Round (Eastern Conference quarterfinal)
Result: 3-2 Pittsburgh
Game-Winning Goal: Petr Nedved
Petr Nedved stepped up in the Pens’ almost 140 minutes of need. The Czech sniper scored the equalizer with 12 minutes left in the third, and he bagged the game-winner with just 45 seconds remaining in the fourth overtime period.
The golden goal was the only overtime winner of Nedved’s career.
The Pens were down 2-1 in the series, so a defeat would have pushed them to the brink. Instead, the Pens tied the series and won the subsequent two games to advance to the second round.
Olaf Kolzig made 62 saves in the heartbreaking loss, while Ken Wregget stymied the Caps in relief of Tom Barrasso, making 53 stops on 54 shots for the famous victory.
The Panthers eventually dismissed the Pens in the seven-game Eastern Conference final.
3. Anaheim Ducks at Dallas Stars (April 24, 2003)
OT Length: 80:48 (Fifth Overtime)
Game and Round: Game #1, Second Round (Western Conference semifinal)
Result: 4-3 Anaheim
Game-Winning Goal: Petr Sykora
Petr Sykora was the hero in the third-longest playoff game in the modern era. On a fresh slate of ice, Sykora scored the winner 48 seconds in the fifth overtime period. The Stars and Mighty Ducks of Anaheim were nine minutes short of playing the equivalent of two and a half games.
The Stars couldn’t come back from the emotional dejection of losing Game 1. Dallas also lost Game 2 in overtime, though that sudden death session ended just 1:44 into the opening frame.
Jean-Sebastien Giguere, who won the Conn Smythe two rounds later, saved 60 of 63 shots, while Turco turned away 50 of 54 shots in the loss.
Anaheim won all seven overtime games during their run to the final. Only the 1992-93 Montreal Canadiens won more overtime games (10) in the same playoffs. However, Anaheim lost the seven-game Stanley Cup final to the New Jersey Devils.
2. Columbus Blue Jackets at Tampa Bay Lightning (Aug. 11, 2020)
OT Length: 90:27 (Fifth Overtime)
Game and Round: Game #1, First Round (Eastern Conference quarterfinal)
Result: 3-2 Tampa Bay
Game-Winning Goal: Brayden Point
The infamous 2020 bubble playoffs saw teams vie for the Stanley Cup on neutral ground (in Edmonton and Toronto) and without fans. Thanks mainly to a 6-2 overtime record, the Lightning won their first of two consecutive Stanley Cups.
Tampa’s first overtime experience was by far the longest, as it stretched to five extra periods against the Blue Jackets in the opening game of the playoffs. Brayden Point scored his first of two overtime game-winners just after the midway mark of the fifth overtime period.
The Lightning fired an absurd 88 shots at Joonas Korpisalo, who miraculously made a record-breaking 85 saves before being beaten by Point’s long-ranger wrister.
1. Philadelphia Flyers at Pittsburgh Penguins (May 4, 2000)
OT Length: 92:01 (Fifth Overtime)
Game and Round: Game #4, Second Round (Eastern Conference semifinal)
Result: 2-1 Philadelphia
Game-Winning Goal: Keith Primeau
Keith Primeau leveled their second-round series against the Pens at two games apiece after over 92 minutes of overtime action. It was the only overtime game-winner of Primeau’s 15-season NHL career.
The Flyers outshot Pittsburgh 72-58 and, had it not been for Ron Tugnutt’s superlative play between the pipes, would have won it much earlier.
The Pens couldn’t rebound from the emotionally ruinous loss and were eliminated after losing the next two games.
The Flyers experienced similar heartbreak in the Eastern Conference final, unraveling after taking a 3-1 series lead, losing in seven games to the eventual Cup-winning New Jersey Devils.
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