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I do believe you have to get expert on all tug of war battles to get the expert medal; however, the tutorial on the first tug of war says you have to clear the board to get expert.  After figuring out a strategy (I'll make a thread for this in a minute) I did clear the board on all the tug of war battles, and still don't have an expert star on the cup on the map for this part of the game. Not sure why. Maybe someone else who has all expert can comment about this as well.