Several times. I also have killed two with one shot. Twice. The first time I shot a big doe in the head there was another doe on the hillside about ten yards above her. The bullet must have defected slightly as it passed through the first deer and hit the other in the chest. She took about ten steps and dropped. I had two antlerless tags so no big deal. The second time there were two does standing directly in line with each other I could see no sign of the second deer until I shot and down went two of them. I took the second one to the game warden and told him the story. He took the deer and had it processed and gave it to the old folks home in our town. I would hesitate to take back to back deer early in the season but towards the end if I have the tags, why not?