No, a truely, absolutely, 100% *perfectly* cloaked object could not possibly cast a shadow. A shadow is an area which is less illuminated due to blocked photons. If photons are bent around the object and then returned *precisely* to their original course, no shadow could possibly result, because the photons would be covering the same region they would if it were not present. They might be delayed slightly by being bent around the object, but that would be undetectable except during sudden changes in overall illumination.
Of course, the counterpoint to this is that the cloaked object would exist in perfect darkness, since no photons would be able to hit any visual receptor it might have. (If they did, a shadow would result!)