A few less common ones I've seen, or done:
A relative had trouble finding the right drain plug---instead, accidentally drained the transmission of a '66 F100, and later screwed up the adjustment of recirculating-ball steering box on his mother's Impala.
A couple of elderly bachelor brothers I knew bought a Chevy Sprint. (It got ridiculous mpg when they drove it from NJ to California and back in summer with no AC.) When the oil filter was stuck, they tried using a hammer and punch on the edge of the filter seam. The punch slipped and punched through the nearby oil passage in the block. Bye, bye, Sprint!
After changing the ArcoGraphite in my Mazda, I leaned the drain pan against the building, to give it time to drain thoroughly into the waste oil jug. While I was napping, water from a thunderstorm poured off the roof, exactly right into the pan and funnel. The rainwater sank to the bottom of the jug, displacing the about half my used ArcoGraphite all over the ground. That was my ugliest oil spill so far.