The amount of juice mainly depends on the size of the pineapple and the type of juicer. If all pineapple sizes were equal, you would extract the most juice from a pineapple using a masticating juicer, which can squeeze out a higher yield. For every 2 cups of chopped pineapple pieces, a quality masticating juicer should be able to extract around 1-1.5 cups of pineapple juice.