Whether it was fortune or not, I was able to snag this trophy on my very first attempt.
Home Run Derby.
Home of the Chicago White Sox - US Cellular Field.
A LH hitter like Prince Fielder is a great choice.
The Bullpen Sports Grill starts at the foul pole and moves towards center field. All you need to do is clear the fence to get the ball into the area needed for the trophy to activate. I found that it took about five swings to get an idea of his tendencies, and from there, was able to hit a popped up pull that landed just past the wall into someone's nachos.
Best of luck!