Top Five NHL First-Round Upsets Of The Last 20 Years

Bolts and Bruins fans, beware.

As the NHL regular season winds down, hockey fans know what's coming next: the long‑awaited Stanley Cup playoffs. Powerhouse teams like the Tampa Bay Lightning , Carolina Hurricanes , Colorado Avalanche , Dallas Stars and others are poised to enter the post-season as heavy favorites, each with a real chance to make a deep run, or even capture the coveted Cup. However, throughout NHL history, hockey fans have witnessed multiple instances of top Cup contenders suffering early playoff exits against teams considerably lower in the standings, sometimes as early as the opening round.

Whether the underdogs went far in the playoffs or were bounced shortly after in the second round, fans always remember where they were when the unthinkable first-round victories happened. Let's look at the top five first-round playoff upsets of the last 20 years, meaning everything from 2006 to 2025 is fair game. 5.

Anaheim Ducks vs. San Jose Sharks (2009) While the Anaheim Ducks had just won the franchise's first and only Stanley Cup in 2007, the 2009 team was in a transition period. NHL legend Teemu Selanne, who was the Ducks' leading scorer in their Cup-winning campaign, was now taking a back seat to young stars Ryan Getzlaf and Corey Perry, both of whom were just 23 at the time.