EVERY Hero Batman Has Defeated
8. Nightwing - Superman/Batman #56
When a version of Batman driven insane by having Superman's powers decides to fight you, there's only one person coming out unscathed; and, spoilers, it's not you.
Despite knowing this, Nightwing goes to fight his mentor, hoping that the Dark Knight's habit of staying out of the light would mean his new Kryptonian powers were weakened.
As it turns out, this very much isn't the case, and Dick Grayson gets beaten to a pulp by his adopted dad instead, culminating in him holding his darling boy miles above the city of Gotham, suspended by his neck.
It's an exceedingly brutal fight, which makes Batman's guilt when he finally loses the powers all the worse, as he's aware that he severely injured the people he cares about just because he got a couple of cool alien space powers.