Boot up a Last Man Standing race and fall to the back at the beginning. Pass ONE car and stay in that position until the car you passed has been eliminated. Immediately pass the next car and do the same thing...stay in that position until the car behind you has been eliminated. Repeat this process throughout the event until you eventually grab the win, along with the achievement.
This achievement can be earned on ANY difficulty setting, so if you're having problems completing it just switch to easy difficulty with visual damage only.