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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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2016 vs. the Pittsburgh Penguins

sid vs. ovi no. 2
May 7, 2018; Pittsburgh, PA, USA; Pittsburgh Penguins center Sidney Crosby (87) and Washington Capitals left wing Alex Ovechkin (8) embrace after game six of the second round of the 2018 Stanley Cup Playoffs at PPG PAINTS Arena. The Capitals won 2-1 in overtime to win the series 4 games to 2. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

The second meeting between Sid and Ovi, again in the second round. Again, it was a hard fought and brutal series, and again the Capitals lost, this time in overtime. The Pens would end up winning their fourth Stanley Cup that year (Crosby’s second) and marked the fourth time they had to beat the Caps to do it.

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