So many for me, but these two are both kinda funny.
Unluckiest (or dumbest on my part!) was just yesterday. In a sunken crypt, I had just smashed up a body pile, when the last man standing – a starred Draugr Archer – got stuck in a muddy scrap pile. He was really low on health so I thought I had him easy, but my attacks (mace or arrows) just couldn't hit him any more. Trouble is, he could still hit me – not fair! I should have run and got my health back, but I started digging to get him out, all the while being hit by his arrows and failing to pay attention to my health – and the b***er killed me. He has now paid the price, but I'm still recovering my grave!
Luckiest (also pretty dumb – there's a pattern to my play!): after a day and a half on my Karve, I sailed between what turned out to be two Plains headlands in the shallows (I'm fairly new to Swamp level, BTW, with Bronze weapons/armour). Night time in the fog and TWO b***dy Deathsquitos started chasing me in the boat (they're active at NIGHT?!). I thought me and my Karve were goners. So I did what I always do in stressful situations and panicked: started trying to shoot them with my bow, before realising I was using the harpoon (laugh as long and hard at this as you wish)! They must've quickly realised they were dealing with an idiot and got bored and left me. Phew!