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?