Yes quak170, if you and your opponent's challenges both have the same seek parameters the server will match you guys up. Of course there are more than 2 people with the same seek parameters so saying that the server will always match you up with a specific person is a bit much :)
Does live chess match challenges?
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I know that you can create a live chess challange, and someone can accept it. But if you create one with the same settings (time control rating range etc.) as someone else's, will chess.com match them up?