On Superstar difficulty vs. the CPU, make two free throws in a row with under two minutes remaining.
Free Throws are what players shoot when they are fouled or once a team gets over the penalty, which means they fouled to many time during the game.
To make this achievement easier set the Quarter Length to 2 minutes before starting the game. Now once the game starts try to keep the game to within 10 and make sure you are winning. If you get to a lead over 10 points the CPU will not foul you. So make sure your lead is under 10 points.
Now once they foul you, you will get either a 1-and-1 or 2 shots. If you get a 1-and-1 make sure you make the first Free Throw as if you don't then you don't shoot the 2nd Free Throw.