I'm a Penguins fan first and foremost (sorry), but my wife is a huge Wings fan and I've liked them enough since I got into hockey around '90.
Some highlights, though some weren't playoff-specific:
- the 08/09 Cup runs vs. the Penguins. Saw many games live including '08 3OT (sadly not the Cup-winning game as my wife couldn't get the time off work), and the '09 Cup win for Pittsburgh. Saw a few Wings wins from those series as well, including the 5-0 drubbing, but those 2 can't be touched. The 3OT game was the best game I've ever seen in person, I wish the Wings would have just won it there. The suspense and feelings brought on by the tying goal in the 3rd, followed by the crazy OT, were plenty for me.
- the 'earlier' Cup wins. While I wasn't in the area at the time and able to watch many Wings games (so I had a lesser emotional stake into it), I was happy to see them do it in my lifetime and also happy for some of the players I'd always been a fan of.
- the Avs fight (wife was at that game, long before I knew her though!)
- a couple personal ones such as meeting some players at the rink (Howe, Datysuk, Lindsay among the best), and my obvious-top choice of proposing to my wife at center ice after a morning practice when the Pens were in town (thanks guys!)
- going to the Winter Classic at UM
Can't really think of any lowlights right now aside from Konstantinov; anything else just pales in comparison. There were things that weren't great, but how can you throw it in with that?