10 Villains Superman Has NEVER Defeated
9. The Batman Who Laughs
Of the many villains Superman has faced in his time, he probably has the worst loss rate against the Batman Who Laughs.
So far Supes has taken the Chuckling Knight on a fair few times, but has never quite come out with that win we've all been hoping for. In Dark Night Metal, the Man of Steel is busy fighting some dragon Jokers (it's a long story) leaving Batman and the Joker to deal with their weird conjoined alter ego. The hero comes closer to victory in the 2019 Batman/Superman crossover, where Superman tries to fool the Hellraiser-esque villain into trusting him by infecting himself with a dose of the chemical that created the chuckling Dark Knight.
Only, as it turns out, the Batman Who Laughs knew he'd do this, due to him having the exact same smarts as our heroic Bruce Wayne. A such, Superman is almost also made evil by the serum, and then has to witness the version of himself that exists on the Batman Who Laughs' world - where he and his family have been killed, and made into a display for the monster to keep as a trophy.
In short, every single encounter between this twisted version of Batman and Superman has led to the Man of Steel getting his all-American ass kicked - and it doesn't seem like things will be changing any time soon.