I have, but, my drain plug is on the top of my kayak, so it really wasn't an issue.
However, one time, I did forget to tie the stringer on good, and when I went to put crappie number 25 on the stringer, it was no longer attached to my kayak. 24 nice specks, to the bottom of the lake. I like to think that someone snagged it later and got a good chuckle out of it.