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1.
the word winfail is used to describe those moments when someone or something fails so hard that it actually wins. winfail can be a noun but it can also be a verb too.
Anchorman on Live News: Keep f*cking that chicken!

Guy: LMAOOO WIIIIIN!!

Buddy: wow. FAIL.

Friend: Oh hoho thats a WINFAIL!
by edyStaaang September 12, 2011
 
2.
A situation that appears to be very awesome (very WIN), but then turns to a very shitty situation (very FAIL).
Dude! Sara is breaking up with her boyfriend...but she says she doesn't want to date for a while...so WINFAIL...
by John Smith74 March 05, 2008
 
3.
When you get a kill in a game, and are subsequently killed immediately after, by whatever means.
"In MW2 I no scoped some douche camper, but then I ran into his claymore, WINFAIL"
by Grand Body March 29, 2010