There are a few scenarios here which I'd classify as upsets. Vulcan Raven isn't even a top 30 for me (although I do like him) but I started voting for him sometimes because, yeah, I admired his supporters.
The Boss falling so early is definitely very much a Board 8 thing; she's definitely a big character not just in the series but the fandom as well.
--
"You caused the rain to bleed." ~SCP~
http://img.imgcake.com/Jeffzeropngus.png "Thanks Punny!"