Cloud > Link 2003
StarCraft > Wind Waker 2004
Knuckles > Magus 2005
Vivi > Mario > Ganodorf 2013
The best one in my mind, to this day, is Vivi > Mario > Ganondorf... maybe not super iconic, but it was such a massive upset I just have to vote for it. The second best is Missingno > Crono, for the sheer hilarity of having a glitch in a contest, but I'm not sure how iconic the upset is, either, and I couldn't fit it in. I think StarCraft > Wind Waker was a more iconic upset than SC > Halo as at least a lot of beat thought it SC would beat Halo. Not so with Wind Waker..... only a few thought it would do it. Not to mention...mass carriers and that big rally.
Leonhart4 posted...
Also the staple LOL X-Stats match is Mario > Samus because that's the match that birthed the phrase.
I thought it was Knuckles > Magus.