Score with a Cheerleader is a quest which is located in the Football Field in Buck to School.
To complete the quest, you must lick one of the cheerleaders in the middle of the field and bring them over to one of the goalposts and take them through the goal, literally scoring with a cheerleader, hence the name. One of the goalposts is the wrong one, and when sending the cheerleader through you will get "Rejection! Try sucking less". This will unlock the Cheer Goat.