Use the same solution TheSinisterDuck posted for the Perfection achievement. Go to
http://www.mathsisfun.com/games/connect4.html to play connect four online. Set the computer to hard, and make sure your turn is first. Now play a single player game against the novice computer lasting only one round. For every move the Xbox AI makes, make that same move as the human player on the connect four emulator. Copy the moves the computer AI makes as your own in the Xbox game. The moves the hard computer AI makes will lead you to victory against the Novice Xbox AI every time. This way you can easily win ten games without using two controllers by yourself or against another player.
Again, credit goes to TheSinisterDuck as I had not thought of using this method until reading the solution for the achievement Perfection. Nonetheless, it will lead you to success here.
Hope this helps as much as it did for me.