Should i report him?
If he pissed you off, just blacklist him, but maybe he entered it before winning the game? Anyways he should care about removing his entry, he can do it later too if he cares, but you should not report him for that, if a guy who owns the game wins it, you can reroll.
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block it manually, there's a little "eye"-icon on the mainpage for every giveaway which allows to permanently block a title (which is damn useful as unfortunately all these "collections" and DLC will not be recognized as owned by the site automatically.
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I'm kinda surprised they don't have a system in place that if you win a game you are automatically removed from other GA for the same title. I guess there is always the chance that the person doing the GA won't give the game, but you do have the chance to win multiple copies especially for some of the games that are popular GA.
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Meh, but do have an interesting suggestion where to place that potato though......
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Well, not likely but it could have been just a honest mistake. I have sometimes entered a ga for a game five minutes after I bought it, just out of reflex (and like a minute before facepalming and removing my entry).
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Might have been using a script to enter giveaways of certain games and not updated it yet.
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Some people automatically enter giveaways with a script, and have no idea what it's trying to win for them. It's not against the rules, other than the "rule" of being a decent human being, perhaps. :)
I suggest checking every time a giveaway ends that the winner doesn't already own the game. Before you send them the gift/key/whatever via email, take a minute to look over their Steam profile. You may also want to take a few more minutes to check they've redeemed all their previous wins... :)
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You should stalk him. Maybe one day he will win two of the same game and you can finally get him suspended!
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On guy entered my GA for game, that he won from me just yesterday. Is it against the rules? He didn't won the second one, so no harm was done. He just pissed me of.
EDIT:
Thanks for your feedback. In most cases i check if winner already own the game. Like i said: no harm was done and looks like he didn't break any rules. Maybe it was jus a mistake. I won't create any support ticket.
And about blacklisting: I really try not to blaclist people for just pissing me off. But I'm weak human being, so sometimes emotions takes control.
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