My longest/flukiest shots in order:
#1 - I was about 13, walking a dyke next to our local slough with my brother and buddy. A teal flushed outta the slough from left to right about 20-25 yards out in front of us and about 25 feet in the air. As the duck passed, I stepped up and dropped it with a single round from my trusty 'ole silver bolted Cooey 22LR....my brother still looks back on that shot and calls it the luckiest shot ever.
#2 - I was 14 and deer hunting with an old Mil Surp 303 british, shot at a nice little 3 pointer at about 125 yards and the calf just back a bit and behind the buck dropped dead...that ole Mil Surp is still around....took some cleaning to get the bore back so it will shoot sub minute of barn!
#3 - Shot a yearling Doe at about 430 yards (estimated) last fall with my new .270 WSM and 140 gr Berger VLD's....first shot was well over her back as I forgot I was shooting a lazer and held too high...second shot hit exactly where I had aimed...double lung! She ran about 60 yards and expired.
#4 - Just last weekend, nailed a coyote at 505 yards (stepped off after the shot, inital estimated distance to be about 475 with the naked eye) with my 22-250 loaded with 50 gr Berger match bullets, held on the second hash mark on my bal plex reticled scope...was actually very lucky as I didn't compensate for the 5mph or so x wind, bullet drifted from a nice broadside chest shot to the top of the neck shot! DRT! Called back in it's companion and missed at about 650 yards....next time I aint missin'!
Best near miss I ever seen was my BIL's shot at a Hungarian Partridge with his .300 Win Mag, bullet hit in front of the bird, send shards of snow and ice through it's body, bullet never touched a feather, but it sure was dead!