Abstract: A vacuum picker apparatus for cups includes a vacuum picker head with concave surface areas, each being preferably ½° reverse angle, and each surface area having a hole therethrough that allows for a vacuum to be formed at the picker head. When the vacuum is formed, the side wall of the cup is drawn, inside the overall circumference of the head at each concave surface area to provide for an effective seal to hold the cup to the picker head, which reduces deformation of the cup and facilitates its extraction for further processing. A protective ring or skirt at the picker head has spaced apart notches through which apertures are formed to direct a thrust of air against the stack to force the stack away from the individual cup being denested. The dual action of the vacuum picker apparatus removes an individual cup from a stack of cups and forces the stack away from the cup to facilitate removal of the individual cup from the stack.