I'm not a big fan of "who would win" or "who's stronger" sorts of pair-offs between superheroes, because it's clear that the victor is just whoever would serve that particular story best. But the scenes in which rarely-paired super-characters square off (like Batman vs Superman or Thor vs Hulk, etc) are often exceptionally fun and memorable, even if they're not definitive.

So I'm wondering, has there ever been a moment in the comics in which Lex Luthor and the Riddler have tested their intellects against each other? They're both often portrayed as almost infinitely intelligent, and lord knows they both have egos to match. It's hard to imagine either being able to resist the temptation of a battle of wits, but have we ever actually seen it play out?

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They have definitely teamed up, but it seems that they have never attacked, fought, or knowingly/willingly plot against each other.

It seems that those times that they have teamed up none has tried to betray each other, so there is no remarkable event or record of one testing intellect (nor fighting skills, nor ability for intricate plans with different layers, betrayals, hidden agendas, contingency plans, manipulating adversaries and/or allies, etc. or the like) against each other.

What I can tell you is that those times that they were teamed up, like in Kingdom Come to name one example, Luthor seemed to have "the upper hand", leading the super-villain gang. This may not probe anything, since Luthor could just have leading skills or charisma that Riddler may lack (after all, and this may actually be completely opinion based, Luthor managed to build millionaire companies and place himself even as president of USA, meanwhile Riddler seems to have a irresistible need of leaving clues for his crimes, make a "challenge" of them, etc. But, again, is not proof of anything).

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