I've had more than one.
First was my first deer hunting experience back in PA. I was using my first deer rifle which was a Rem 243 with iron sights. I was up in a tree stand and a 3x3 buck is coming down the trail and stops about in front of me. It was a front slightly quartering shot about 45* down almost right below me. I decided to take a head shot since he was so close and the rack wasn't anything special. I fired and he turned and ran off much to my surprise and dismay. I got down and found a good bit of frothy blood so I figured the bullet went low and probably went through the jaw and trachea. Not sure why it went low other than my sight height was a little over an inch above the bore. So I proceeded to track it down off the wooded hill to where it went into a country club. I got permission to follow into the club by a security guy who was driving by and tracked it through the golf course which was closed for the season. Came to a stream and the blood trail was getting very sparse. Crossed the stream, no blood. I search up and down, still no blood, so I started back and ran into another guy who was also on the trail. He said let's go back and see if we can find him. There was a stand of trees that he thought the buck might have gone in to and he was right. Kicked it out and gut shot it on the run with his 220 B and it ran into another stand of trees at the other end of the club next to a residential sub-division. I posted on one end and he pushed up through from the other end. Here comes the buck with it's bloody tongue hanging out and stops about 15' from me broadside. I should have drilled him through the shoulder but put one through the ribs at point blank range. The buck bolted and ran out of the woods into the sub-division and some lady started screaming "you hunters....." We unloaded our rifles and walked out onto the street and I felt like crap. We couldn't very well track it anymore through everyone's backyard. 2 days later up in the same stand, a small spike walks under and I drilled it through the lungs and heart. It ran down hill to the toward my truck and piled up.
Next, antelope hunting
in Eastern Montana. Back in camp for lunch with a couple of my hunting buddies and here comes a small band of goats by the camp at less than a 100 yds. I had a doe/fawn tag and an either sex (buck tag). No Bucks, so I decide to shoot a doe. Up with the rifle, crosshairs on target and let it go. Down with the rifle and one doe is down and another is moving very slowly while the rest of the band is bolting off. Looking closer, I can see intestine dragging from the offside of the other doe. Realizing what I had just done I put the rifle back up and finish her off. Gut them and drag them back to camp. One of my buddies was nice enough to put his doe tag on one of the does so I could still shoot a buck. Needless to say it was more than a little embarrassing and a big lesson learned about shooting into multiple targets.
Next, cow elk hunting during extended late season about 5 years ago. After walling around most of the day I found a good size herd feeding in sage pasture. I was just inside the edge of the trees and put a stalk on and finally crawled up behind some sage to about 150-200 yds away from the nearest cow. I did not have a rest for the rifle and am usually pretty good offhand or off the knee. The rifle was a newly purchased SAKO Finnlight 300 WSM
that was a very disappointing 2 MOA shooter but the only operational rifle I had at the time. Still, inside 200 yds I should easily be able to put one through the kill zone. I put my elbow on one knee and attempt to place the crosshairs on target but having a little difficulty holding steady. I do my best and take the shot and the cow goes down. I walk up and can see it is thrashing around, with back legs paralyzed. I put one through the head to finish her. The first shot struck the lower part of the spine just behind the last rib, about 2' from POA. Next time, take a little more time to settle down for a good steady shot.