METAL WOLF CHAOS XD

Stomp with A to jump then Y to stomp. This is first available on Mission 2, San Francisco. On the first set of targets (marked by the word target above them), I was able to get this on the target to the left.

Many of the Targets in the game cannot be destroyed in a single stomp. Luckily, in Mission 2: San Fransisco, at the end of the mission there is a large building covered in "Target" markers. Just run up to it, jump in the air and hit and you should destroy several and collect this achievement.