Twice, but both were with a rifle.
Last fall I had a nice 8 point show up out of no-where ata brisk walk and didn't have time to turn so I had to take the 95 yard shot left handed.After the shot, he just trotted over the ridge finger that I was on and I thought I'd missed him. Ihopped up on the seat of the ladder stand and saw himstop and stare at mefrom 150 yards while presenting me with a quartering away shot. I drilled him through the heart and he dropped. Found out when I recovered him that the first shot blew through the liver.
The other was the first buck I ever killed. I was using an old Winchester 30/30 with no scope. It was FREEZING, and I was hunting on the ground. I'd leaned the gun against a tree and had my hands stuffed inside my coveralls trying to warm them when he showed up over the ridge only 30 yards away. He knew I was there, but didn't know where. After about 5 minutes of playing the "move slowly when his head goes behind a tree and freeze when he's looking" game, I finally got the gun up to my shoulder. I pulled the hammer back and, of course, the "click" might as well have been a brick being dropped. He went on full alert and I shot quickly, and watched the deer literally spin a complete 180, and take off. Somehow, I'd completely missed the vitals, the gut... the entire body cavity. The bullet had passed just below the spine above the hindquarters and severed the artery. I found him less than 100 yards out. My first field dressing lesson was by far the least messy.