Jamie Langenbrunner's red line slap shot that went in on Chris Osgood during OT in game 5 of the 1998 WCF comes to mind.
Certainly helped fuel the silly notion that the Red Wings won in spite of Osgood in 1998...
I think it is about time to exhibit some of the weak goals Osgood let in during the 1998 playoffs:
Round 1 - Game 3 against the Coyotes he lets in a long distance one to Roenick that trickles through
Round 2 - Game 3 against the Blues he lets in a centre ice blast from Macinnis in the last minute that sent the game to OT. To be fair Macinnis did get all of that one.
Round 3 - Stars live another day with a centre ice goal in OT by Langenbrunner (who is no Al Macinnis). It is obvious by this point that teams are taking slap shots from anywhere on Osgood.
I would add a fourth one in this post if I was allowed to.
To Osgood's credit he bounced back with remarkable games after those ones. His resiliency is why the Wings continued to have faith in him....that being said, those are some of the weakest compilation of goals you will see against one goalie during a playoff season (not to mention at crucial junctures).