My little brother shot a raccoon I had trapped this summer, and the first .22 between the eyes just pissed it off. Scared lil' bro half to death, and sent him sprinting to grab another .22 to stick in the single-shot bolt-action to finish the job.
It took 3 shots.
It is kind of amazing how they are still somewhat aware after a shot between the eyes. After the first shot they typically hide their head under their body and twitch and shake allot. It make the 2 nd shot tough.