(1)Okay so I would have an Alakazam. They have an IQ of over 5000, so there's no doubt it would rival superman and his immense brain power. They are also psychic types for superman’s weakness to magic. It also has the ability Magic Gaurd, which prevents indirect damage so Super Man can only take it down with a direct attack. Next, there’s Clefairy. Being a fairy type, fighting type attacks are useless against it. Chances are, superman won’t know this and attempt to attack Clefairy anyways.
Because of its ability, cute charm, Clefairy has a 50% chance of enticing Superman with its cute charm that Superman would feel conflicted and not attack Clefairy half of the time, giving it plenty of opportunities to get at him. My next pokemon are Gengar or Houndoom to get poison and dark type attacks to weaken Superman/’s powers with. Gengar’s poison might act as radiation to drain his powers. Houndoom’s dark type attacks will negate his sun based powers. Next is Jolteon with rain dance. Rain makes electric type attacks never miss the opponent, so if Superman somehow regained his powers after Gengar/Houndoom he can’t use his speed to excape Jolteon’s Thunder attacks.If all else fails, I’ll send out Tyrogue. Being a baby pokemon, Superman might feel conflicted attacking it being an infant and all. I might also play the as underdog, Best case scenario Superman is so amazed by the pokemon’s confidence he takes a dive for the small fighting type pokemon with big dreams.
This strategy would honestly probably work. Superman would, upon seeing he's battling a baby pokémon, forfeit the fight entirely.
But I also want to point out that you're employing basically the same strategy Batman used to beat Superman in The Dark Knight Returns. Drain superman's powers (in that situation, a kryptonite-tipped arrow fired by Green Arrow, in this case, using poison to replicate the effects of green kryptonite), keep them from regenerating by blocking out the sun (in that situation, a nuclear bomb kicking up a cloud, in this case, Houndoom casting dark), using a powerhouse to weaken superman (Batman's exosuit, Jolteon's electric attacks), then appealing to his moral compass to force surrender (fake heart attack, baby pokémon).
