Doomed to Repeat
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The Capitals have a history of losing to the Penguins in overtime in the playoffs. That has continued in this series -- they have fallen twice, dropping their all-time record to 1-7.
| Year | Game | Result |
| 1991 | 2nd round, Game 2 | Penguins, 7-6 (OT) |
| Capitals rallied from two down to tie, but lost on Kevin Stevens's OT goal. | ||
| 1995 | 1st round, Game 5 | Penguins, 6-5 (OT) |
| Capitals led twice in the third period before falling in OT. | ||
| 1996 | 1st round, Game 4 | Penguins, 3-2 (4 OT) |
| Olaf Kolzig made 62 saves, but Petr Nedved scored the game-winner. | ||
| 2000 | 1st round, Game 2 | Penguins, 4-3 (OT) |
| Jaromir Jagr scored less than a minute into an OT power play. | ||
| 2001 | 1st round, Game 4 | Capitals, 4-3 (OT) |
| Jeff Halpern scored 4:01 into OT for the Capitals' only win in such games. | ||
| 2001 | 1st round, Game 6 | Penguins, 4-3 (OT) |
| For the sixth time in eight years, the Penguins ended the Capitals' season. | ||
| 2009 | 2nd round, Game 3 | Penguins, 3-2 (OT) |
| Kris Letang goal 11:23 into OT snapped Caps' 5-game playoff win streak. | ||
| 2009 | 2nd round, Game 5 | Penguins 4-3 (OT) |
| Evgeni Malkin scored the game-winner with one second left on the power play. |