Can you put a 2000 or newer wheel on a 1999 Ultra like the one below, by just switching the bearings if you have the right rotors for the wheels?

 

You must have the correct rotors to fit over the rotor sholder. The timkon taper were too small so your origional rotors are too small. This is what you need minus the 2000-2001 inside. You must use a spacer. I made this page so members could visualize the problems one face's if going down in years. You face no problems going up in years. LINK: is below, just read it. Good luck
http://motorcyclemetal.com/subpage16.html