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8 times the Washington Capitals lost in the playoffs to the eventual Stanley Cup Champion

The Capitals have a long and tortured history when it comes to playoff loses and heartbreak, but nothing stings more than the fact that the franchise has lost to the eventually Stanley Cup Champion eight times in their playoff history.
ByJohn Murray|
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Apr 12, 2026; Washington, District of Columbia, USA; Washington Capitals players celebrate after their game against the Pittsburgh Penguins at Capital One Arena. Mandatory Credit: Geoff Burke-Imagn Images
Apr 12, 2026; Washington, District of Columbia, USA; Washington Capitals players celebrate after their game against the Pittsburgh Penguins at Capital One Arena. Mandatory Credit: Geoff Burke-Imagn Images | Geoff Burke-Imagn Images
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2009 vs. the Pittsburgh Penguins

Ovi vs. Sid no. 1
Apr 30, 2016; Washington, DC, USA; Pittsburgh Penguins center Sidney Crosby (87) and Washington Capitals left wing Alex Ovechkin (8) follow the puck in the first period in game two of the second round of the 2016 Stanley Cup Playoffs at Verizon Center. The Penguins won 2-1, and the series is tied 1-1. Mandatory Credit: Geoff Burke-Imagn Images | Geoff Burke-Imagn Images

This was the first ever Alex Ovechkin vs. Sidney Crosby playoff series and it was a doozy. The series is famous for the dueling hat tricks. The Caps won Game 6 to force game 7, only to get blown out 6-2. Pittsburgh went on to win their third ever Stanley Cup, the first in the Crosby/Malkin era. This was also the third time the Penguins beat the Capitals on their way to winning the Cup.

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