You bet you can. My dad and uncles took a trip down to Texas about 6 or seven years ago and they came across a deer with a broken back leg. They said they wanted to dead so they had my dad shoot it with his .22 ruger right in the forhead. I wasnt there but he said it didnt even flinch.Also 2 years ago i shot a ten point that was bleeding from it eye. I figured it lost it in a battle but when i took a closer look there was a small bullet hole behind it ear. It was a very small hole probably from a .22 of some kind of varmit gun. The buck was still chasing the does around when i took him. The wound was still bleeding so it was fresh, most likely caused by a poacher. So to answer your question it all depends on what anlge the bullet takes.