I dug a little more using the Wayback Machine.
A yoyojam.com products page capture from February 29, 2000, does not have any tops. One from September has them, including the bearing version of the Top Dog:
YYJ September 14, 2000. Jon had won Worlds a month earlier using a Top Dog, but I am not sure if it was bearing. Unfortunately, I did not find relevant page captures between February and September. I guess Jon or Valerie should be able to tell us when they came out.
Doing the same with Duncan (yo-yo.com), the products page from March 4th of 2000 announces the Storm Series "coming this Spring to a store near you". Unfortunately, Duncan was already using all flash sites that don't capture well.
I think it is not yet settled if YYJ or Duncan started selling bearing tops first.
Not even close to the first bearing top. I just saw a Pop's Top that was wooden with a bearing. Apparently you can say whatever you want in copy as long as YOU believe it's true.
The Pop's Top may be a bad example. I don't have one yet, but from what I have been told the tip does not spin in spite of what the box says. I do have several other wooden tops that do have bearing tips, but almost all are the ballpoint pen type: the bearing will let it spin longer on the hand but not on the string. If we are talking about modern bearing tips, it's main advantage is longer spins on the string. I do have one old top circa 1930's, I believe German, that actually has a radial ball bearing like a modern top. But even that one does not have a very nice tip for tricking.