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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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1991 vs. the Pittsburgh Penguins

The Penguins greats: Lemieux, Francis, Jagr
Feb 18, 2024; Pittsburgh, Pennsylvania, USA; Pittsburgh Penguins former right wing Jaromir Jagr (middle) greets teammates Mario Lemieux and Ron Francis during a ceremony to retire the jersey number of Jaromir Jagr at PPG Paints Arena. The Penguins host the Los Angeles Kings after the ceremony. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

The Caps were fresh off their first conference finals appearance in 1990, when “the Druce was Loose!” After they dispatched the Rangers in round one, they faced the absolutely LOADED Pittsburgh Penguins team in the second round. Nine Hall of Famers played on that team, many of which are some of the greatest hockey players to ever play the game: Mario Lemeuix, Ron Francis, Jaromir Jagr, Bryan Trottier, Paul Coffey, Larry Murphy, Mark Recchi, Joe Mullen, Tom Barrasso. The Capitals didn’t have a chance and lost in five games and Pittsburgh went on to win their first ever Stanley Cup.

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