I would like to see a GM get beaten by an "armature" myself sometimes ;)...
Biggest Fail in Chess

One of the higher profile ones I can think of is Kramnik missing a mate in one vs. Deep Fritz:
http://en.wikipedia.org/wiki/Blunder_(chess)#Deep_Fritz_vs._Vladimir_Kramnik
There's a longer list of other examples on that page as well.

very nice to write "Checkmate!" there in the anotations, I guess most of us wouldn't have realized it.
lol

What is the biggest fail in chess history? There is the fastest mate that’s possible in a chess game (the easiest answer). But is there a game where one player had a winning position and completely messes it up, a game where a grand master is beaten by an armature, or when you are simply embarrassed on the chess board and mocked forever as an idiot. Post on this forum the biggest fail in chess history.
This forum.
What is the biggest fail in chess history? There is the fastest mate that’s possible in a chess game (the easiest answer). But is there a game where one player had a winning position and completely messes it up, a game where a grand master is beaten by an armature, or when you are simply embarrassed on the chess board and mocked forever as an idiot. Post on this forum the biggest fail in chess history.