Most crushing losses by Detroit Red Wings in past 3 decades (VIDEO)

Throughout the near 95 year history of the Detroit Red Wings, generations of fans have been treated to some of the greatest moments and players in sports history. Detroit’s is among the most passionate fan bases in the country, and are the driving force behind the area affectionately being known as “Hockeytown”.

And while we’ve enjoyed some immense highs over the years, there have also been unfortunate moments of heartbreak.

Let’s take a look back at some of the crushing moments that fans of the legendary franchise have endured in the past three decades.

Blown away by the Leafs

The Red Wings anticipated a long playoff run after they compiled a 103 point regular season, led by Captain Steve Yzerman’s 137 points. Instead, they found themselves headed for an early summer following a 7-game opening round upset at the hands of their Original 6 rival Toronto Maple Leafs. Nikolai Borschevsky tipped in future Red Wing defenseman Bob Rouse’s pass past goaltender Tim Chevelde in overtime of the deciding game, ending what was a promising campaign for Detroit.

Death by Sharkbite

The Red Wings were once again stunned in the first round of the Stanley Cup playoffs after cruising through the regular season. A second consecutive opening-round 7 game loss added to the growing list of disappointments that Red Wings fans endured since they’d last seen a Stanley Cup victory in 1955. San Jose’s Jamie Baker firing the puck into the open net following a miscue by young goaltender Chris Osgood broke a 2-2 tie in the 3rd period, leading to yet another early exit for Detroit. Osgood was in tears in the team dressing room afterwards.

Burned by the Devils

The lockout-shortened 1994-95 season saw the Red Wings once again cruise through their regular season opponents and the first three rounds of the Stanley Cup Playoffs, earning their first trip to the championship round since 1964. However, they ran into a trap called the New Jersey Devils, who swept the favored Red Wings in a stunning four-game series.

Snowed in by the Avalanche

It finally seemed as though it was all coming together. A record-setting 62 victory regular season and a second consecutive trip to the Conference Finals had the fans of Hockeytown believing it was finally their year. However, what followed after Captain Steve Yzerman‘s dramatic 2OT game-winning goal in Game 7 of the previous round would set the stage for arguably the most bitter rivalry in sports. The Colorado Avalanche, playing in their first season following relocation from Quebec, earned a 6 game win over Detroit that was overshadowed by the horrific hit on Kris Draper by goon Claude Lemieux. Once again, Detroit was headed for an early summer.

Fowled by the Mighty Ducks

The stage was set for another Stanley Cup run. The Red Wings entered the 2003 Stanley Cup playoffs as the #2 seed in the Western Conference and were intent on defending their title. Instead, the upstart Mighty Ducks of Anaheim had other plans. Led by a superhuman performance in net by goaltender J-S Giguere, Anaheim pulled off a shocking sweep of Detroit in four games.

Slipped up by the Oilers

Stop us if you’ve heard this one before – a dominating regular season by the Red Wings that ultimately ended in an early exit from the playoffs. Once again, this bitter pill was swallowed by Detroit after cruising through the regular season only to see their campaign end at the hands of an upstart team. This time, in the form of the Edmonton Oilers, who would eventually advance all the way to the Stanley Cup Finals as the #8 seed in the West.

Frozen by the Penguins

The Red Wings had their eyes set on a second straight title, and even added reinforcements in the form of sniper Marian Hossa, who joined Detroit to earn a Cup ring after having lost to them in the Finals with the Pittsburgh Penguins just weeks before. Despite a shaky defensive regular season, Detroit once again advanced to the Stanley Cup Finals, where once again, the Penguins awaited. Detroit held series leads of 2-0 and 3-2, but saw them both slip away. The deciding Game 7 in Detroit was defined by two goals from Penguins gritty forward Max Talbot, as well as a last-second diving save by goaltender Marc-Andre Fleury on Nicklas Lidstrom as time expired. Detroit was then forced to watch as Pittsburgh skated the Stanley Cup on Joe Louis Arena ice.

Clipped by the Blackhawks

After an exciting 7-game series win over Anaheim, the Red Wings found themselves matched up against their Original 6 rival Chicago Blackhawks, whom they took a 3-1 series lead over. However, Chicago would storm back with three straight victories, including a heartbreaking overtime win in the deciding Game 7. Defenseman Brent Seabrook‘s seemingly harmless shot was deflected by Niklas Kronwall past a startled Jimmy Howard, ending Detroit’s upstart run.