I have had 2 occasions where I made horrible shots on deer. First time I chaulk up to inexperience, It was my first year hunting deer, I was excited when a doe came out in the field on the first evening (remember this is the first day I ever hunted deer) I was hunting with a 30-30 3X scope. I figured about 150 - 175 yrds away so I up and fired. She spun in circles a few times before leaving the field.....wasn't too sure what to think about that,,,,,went down and started looking around.......no blood around at all. Father showed up and we started seeing a drop or 2 of blood then we found her bottom jaw laying on the ground right where she entered the woods.........we searched and searched....no luck.....GOOD ENDING....another hunter shot her the next morning....I felt horrible that night and still do but glad that she didn't starve to death due to me shooting her jaw off.
2nd time was me shooting at a deer that was out of range for the gun I was using....I shot and didn't realize that the doe was as far as it was..(300 savage). hit her low and we looked all day.....blood trail just stopped.....that was wk 1 of the season.......I ended up seeing her later in the season with a bad limp........so I shot her.

I got very lucky 2 wounded deer and both ended up being killed in the long run.....could have ended much worse........since then I have never missed a deer and have not had to search more than 50yrds for them..........KNOCK ON WOOD