After you complete the scouting games and get drafted in Road to the Show, you can unlock this in your first minor league game. At some point in the game, you'll be prompted to select which challenge you want to attempt to complete. All you have to do is fail the challenge.
For instance I was a starting pitcher and I had to select if I was going the get the batter out on a pitch high in the zone or low in the zone. I selected high and pitched it low instead.