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1.
A shitflip is to attempt to kickflip or heelflip or any other flip but have the board completely fly away from you when you kick thus causing embarrassment and making you look like a total dork.
We've all done shit flips. :D
Skater 1: "Duuuuuude check out this sweet quad kickflip."

Skater 2: 'Yeah right, lets see it."

Skater 1: -board flies 20 feet away, gets run over by a car-

Skater 3: "wow what a loser."

Skater 2: "yeah i know right, that was a total shitflip."
by ccchhhrriiisss December 29, 2007
 
2.
a skateboarding maneuver involving falling on one's ass and/or face, is generally very embarrassing. immediate side effects are bruises and cuts, long term effects include fractured egos and loss of soul points.
i ollied over that bench and then shipflipped right onto my ass
by sirsurefoot April 23, 2005