20 years would table all the way back to maybe including 93 until we start the next season. Losing a cup stings a lot, but we got steamrolled in 95', by the time the dust had settled it didn't hurt as bad for me as other losses, it might not even be top 5.
93' Toronto Game 7 overtime, brutal, rival everything imaginable sucked about this
94' Was at this one in person Sharks that was awful, people were throwing away their jerseys at the Joe
96' In many ways when it happened the toughest I have taken one. Remember thinking Draper's career was over, we are never going to win and this team is cursed. A why do you do this to yourself, why root for this team? They terrorized the league that season, were ridiculous, that was very hard to take in the moment. Those of us that believed in 94-96 that it was our time, were starting to feel like Canucks fans now, something wasn't right and did we just miss our time?
06' Knowing it could be Yzerman's last moment made that one brutal. You could feel it and even if he was declining and you knew he was too hurt to continue, it tore your heart out watching him disappear into that tunnel in Edmonton after a pathetic series by pretty much everyone but the Captain.
09' Game 7, don't want to lose a Game 7 of the Stanley Cup finals, would rather get hammered like the Devils did. The fact Crosby would enjoy so much praise while he sat on the bench with a freaking charlie horse made this one more annoying. But we didn't close and the team likely cost Osgood a Conn Smythe and a locked position into the HHOF. I hope he still gets in, but that was a part of the suck that night on top of just not winning. At least I will always remember that angle.
13' Of course this year blowing a 3-1 lead to our second biggest rival. It hurt but we shouldn't have won the series.
A lot of what has made the Wings playoffs exits pretty bad is of course they are bad as die-hard fans, but also we have no reason not to believe this thing isn't ending on Woodward Avenue.
At the time it was easily 96', there is a reason we hated that team so much, it started there, it started with the bitter feelings over how that played out. It would spark one of the greatest conflicts/rivalries in sports, but if you weren't mad as hell after that series you were very unusual Wings fan. Tough way to end that season, in a lot of ways even tougher than Game 7 in the Stanley Cup finals at least for me given Draper's ongoing status updates and the immaculate season the Wings had, putting them in the position to claim greatest team ever if they pulled off that victory and Cup over an easily beaten Florida in the next round.