Fume Knight was my bane back in the day, took me so many attempts to perfectly time my rolls and chugs. It wasn't so much he roll caught me a lot, but punishing my heels and one shotting me.
Fuck Sinn, cunt broke my weapons. Other then that, eh?
Kalameet certainly is in my opinion the second best dragon fight. Midir is my favorite. I never really found him that difficult, there was a time when Nick couldn't beat him solo but eventually he did it.
Gwyn, parry ez. Without parry, still ez with a fast weapon.
Flame Lurker still haunts my nightmares... oh wait never mind I have my water spell and/or flame resistant shield.