Odious, hateful, or detestable; causing feelings of anger or resentment.
彼のずる賢さが本当に憎らしい。
His slyness is truly hateful.
憎らしいほど簡単に成功してしまった。
He succeeded so easily it almost makes you resent him.
憎らしい顔をしていると誤解されることがある。
Sometimes people misunderstand and think you look hateful when you have that expression.
(Ironically) used to mean something like 'so cute/adorable it's almost annoying'; said with affection or teasing.
憎らしいくらい君は元気だね。
You're annoyingly energetic (in a teasing/affectionate way).
子どもが憎らしいほど無邪気に笑った。
The child laughed so innocently it was almost aggravating (in a fond way).