As already stated, Hal Jordan Parallax back in Zero Hour might probably the biggest lose. One smack. I don't really count Death of Superman as a defeat since both "died" and got resurrected from the fight anyway. That was a stalemate. One clear defeat of Superman was against Atlas where he needed to be saved by Krypto. Other people who's beaten him are the team busters: General Eiling (beat Superman along with JLA), Despero (also did beat Superman with JLA), Emoboy Prime (beat Supes alongside a lot of heroes... temporary loss though cause they eventually won both Infinite Crisis and Sinestro Corps War), Ra's Al Ghul (beat Supes alongside JLA using Batman's plans), etc.
Non-Canon: Batman in The Dark Knight Returns
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