Start by using a food processor to crush the oreos. Set aside.
In a large mixing bowl, beat cream cheese and butter for 3 minutes. Add powdered sugar and vanilla and beat an additional 2 minutes, scraping down the sides of the bowl as necessary. Remove a spoonful (about 2-3 Tbsp) and place in a small piping bag. Set aside.
To the bowl of cream cheese, add chocolate syrup and crushed Oreo cookies. Blend completely.
Line a large bowl with plastic wrap. Drop the cream cheese mixture into the plastic wrap lined bowl. Fold up the plastic around the cheese ball. Refrigerate for about an hour.
Remove plastic wrap and shape the cheese ball into a football on a serving plate. Press chocolate chips into top and sides until completely covered. Using your reserved cream cheese mixture, snip off the corner and pipe "laces" onto your cheese ball.