Far from a deer, but when I was young I saw my Dad shoot at a crow in field about 150? yrds away. We could only see it`s head and neck sticking up from behind a small knob. He shot, the crow dissapeared. When we picked the bird up, his eyes were bulged out of his head...but not a mark on em. 250/300 using an 87 gn bullet of some make. FWIW.
