I've done it once on a buck that had a small rack, but i know had to be at least 2.5 years old dressed weight was 140.
It was my first ML deer. I was hunting private land in Wilson County and I had been sitting in this stand through out bow season, and seeing deer, but they would never use the trail that I set up on right in front of my stand. I had just really started to take hunting seriously and was learning as I went, so I believed most of what I read in magazines and saw on hunting shows. I got to the land late (right at legal light) and pulled up to two small bucks standing where I park at the edge of a field. They ran off into the field but stopped and started sparring. I couldn't see them, through the scope and they trotted off down into the woods. I walked in as quietly as possible and got up in the stand. Once I got settled I could see the two deer I saw up top on the field, off to my right going away towards another property. I settled in and within 2 minutes i heard something over my right shoulder behind me. So like a true amateur I snort wheezed, because a TV show said it would bring them right to me. Well i kept hearing it and soon enough i could see a buck to my right down the trail i was sitting on about 75 yds out just eating leaves on trees. I'm right handed, so I stand up (no safety harness, so i'm nervous) I aim shoot, the smoke clears, and this buck is sitting there, looking around then starts eating again. I start to reload and I realize he is now walking up the trail and will be walking in front of me momentarily. I'm fumbling around, trying to reload (did I mention this is my first ever ML hunt) and watch him at the same time. I get the powder and bullet seated then have to open the breach to change out the 209 primer. I get it done and he is now pretty much in front of me just a bit to my right at 30 yds. I aim, shoot, he jumps 3 feet straight up, lands, and just stands there. I start freaking out, and trying to reload and I see him start to wobble and then I see the blood on his side and he just goes stiff leg and tips over (never seen a deer do that before or after that). I heard him take his last breath and sat down. no sooner than i sat down a 4 pt runs in to investigate sees him and runs out. then I hear something else coming off my right and it is two coyotes. I realize I never changed the primer, so I go to do that and they bust me. the big male is out, but the female circled into the woods and starts to make her way right down in front of me to a clearing, which she will have to cross to get to my deer, which is about 20 yds from her. I get the primer in and she steps out. BOOM! yote down!
I got down and went and got my buck and yote. FYI this all occurred within 20 minutes of me leaving my truck.