The award for the most unlikely ES goal in the playoffs (yes, we have a metric for this) occurred in Game 4 of Detroit-Columbus, a high scoring back-and-forth game that the Red Wings ended up pulling out 6-5 for the series sweep:
http://www.nhl.com/ice/recap.htm?id=2008030164
Unlikely considering the otherwise poor postseason offensive rates of the Blue Jackets on the ice -Rick Nash, Kristian Huseluis, Manny Malhotra, Fedor Tyutin, Rostislav Klesla, Steve Mason- and the otherwise excellent defensive rates of the Red Wings on the ice -Pavel Datsyuk, Marian Hossa, Tomas Holmstrom, Niklas Kronwall, Brad Stuart, Chris Osgood.
If you take a look at the video of the goal -at 1:44 of the 2nd period- you can see a clever thread-the-needle pass by Tyutin from the blueline to the high scoring Nash for an easy tip-in at Osgood’s left. Overall, Detroit doesn’t seem to have a high sense of urgency in the sequence, with a 3-1 lead in the game and up 3-0 in the series. Stuart and Osgood seem to both be caught napping by the quick pass to the cutter.
A key to scoring in these unlikely situations is an isolated play with one or two quality players on the lower quality side taking quick advantage of an opportunity, neutralizing the overall talent gap on the ice.
Thus, not surprisingly, the most unlikely goal in a later round was basically a one man show – More on that next time.