Since you're going to be taking peoples' money, and basically giving out a 'prize' to the competition winner, it'd be pretty much like running an online poker site or something similar. And they have a LOT of stuff to take care of where the law is concerned.
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Not at all, it is not gambling. Poker is. The game is not randomised and does not rely on luck to win. Your $5 pays for the game and is not a stake.
This is not considered gambling and therefore would not break any laws.