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When two events coincide in the course of attempt to correct one fail leading to a second fail in which both parties are unable to continue due to shame.
An example of a failmate would be if a group of thieves stole a car with no wheels, then the cops who came to get them hit the parked car. The double fail means that no beneficial conclusion can be reached by either party without suffering epic shaming.
failmate by Chez guevara February 5, 2009
Related Words

Failmageddon 

Failageddon is a massive spam of wipes,lost battlegrounds or any other sorts of fail in any MMORPG (especially WoW).
<player 1> Man,we wiped 17 times on Thaddius in Naxx 25 today!

<player 2> What a failmageddon :O
Failmageddon by Uber Failz December 24, 2009

Failmaster 

To suicide in Super Smash Bros.

Inspired by a wolf using his final smash, only to fall through the stage and die with his landmaster.
"You just failmastered."

"FAILMASTER!"
Failmaster by FernIH April 6, 2008
When opposing forces fail to resolve their differences but successfully turn away their supporters in the process.
The Two Party System has resulted in a failmate for the Citizens of the United States of America.
Failmate by cRitterology February 23, 2009
Failmail is the pinnacle of failure or the result of a consistant string of failures and is often used to describe someone else's helpless situation
"He's got failmail!" to describe someone in the process of failing

in a different context "What's wrong with him?" "He just recieved some failmail" or "some failmail just arrived in the post"

or can be used as an insult; "Thats a terrible idea, check your inbox for some failmail you bad"
Failmail by SabaJamal June 3, 2009
The email that you send and then realise that someone was copied in who shouldn't be.
From: Darren
To: James
CC: Karen
Subject: Karen

Don't you think Karen is a total slut?

From: James
To: Darren
CC: Karen
Subject: RE:Karen

Failmail dude...
Failmail by Jaybone_81 January 21, 2010