Joel,
It does sound like a difficult case. I agree with a lot of what Ben said. Possibly asking the child "if your mother (or whoever referred him) were here what would she say?", "what do you think that your mother would want you to work on?" "How do you feel about your mother bringing you here?" If you start getting an emotion out of him (which I am guessing will be anger) then you have your foot in the door. "What about ____ makes you feel angry?" "When you think about ____ what are some of the ideas that go through your mind?"
But.... on the other hand, if he still doesnt give anything then you could either 1. Tell him something like "if I were failing all of my classes, I think I would be feeling pretty mad or sad. Are you feeling this way?" He replies "no". "Well, then we are obligated to spend this hour together for the next few weeks, what would you like to do during our time."
Even if several of the first sessions are just spent playing games, you are building rapport with him and he may start to discuss how he is feeling about things.
Or...2. You could ask whoever brought him (mother, father, whoever) to come in on the session. In the presence of the kid, ask mom why she brought him here, etc. You may start seeing some emotion out of him then, and may be able to start working on some issues.

In the end, my initial thought is that this kid is used to failing and has subsequently "cut" himself off and has disconnected from things so that he will not be hurt. He probably sees you as just another person to tell him what to do and to remind him how he is such a failure. I think reestablishing a connection (by building rapport with him, and working on his relationship with his parents- who are probably adding to his feelings of being a failure) are key, In addition to working on his self defeating beliefs. What may also be helpful is to focus on things he is doing well (what has he succeeded at, how did he feel, what did he do, what were his thoughts, etc.) By using a more 'balanced approach' between 'problem talk' and 'solution talk' (as my solution focused therapy friends would say) it may help him overcome his belief that he is a failure at EVERYTHING and that he will ALWAYS fail.

Just some guesses,Hope this helps, good luck

Micah