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Five Longest Playoff Overtime Games The 5 longest overtime games in Stanley Cup history. Note the following Series initials: SF (semifinals), CQF (conference quarterfinal), CSF (conference semifinal), DSF (division semifinal), QF (quarterfinal) and Final (Cup final). Series winners are in bold type; (*) indicates deciding game of series. | | | OTs | Elapsed Time | Goal Scorer | Series | Date | Location |
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| 1 | Detroit 1, Montreal Maroons 0 | 6 | 176:30 | Mud Bruneteau | SF, Gm 1 | 3/24/1936 | Montreal | | 2 | Toronto 1, Boston 0 | 6 | 164:46 | Ken Doraty | SF, Gm 5 | 4/3/1933 | Toronto | | 3 | Philadelphia 2, Pittsburgh 1 | 5 | 152:01 | Keith Primeau | CSF, Gm 4 | 5/4/2000 | Pittsburgh | | 4 | Anaheim 4, Dallas 3 | 4 | 140.48 | Petr Sykora | CSF, Gm 1 | 4/24/2003 | Dallas | | 5 | Pittsburgh 3 Washington 2 | 4 | 139:15 | Petr Nedved | CQF, Gm 4 | 4/24/1996 | Washington |
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