Originally Posted by faultfoot
That said, does anyone know if Federer even played in the 99 AO or USO?
No, he did not play in either.
His ranking was around #300 at the time of the '99 AO so he may not have even played the qualies. He was ranked #106 around the time of the '99 US Open so he probably just missed the cut-off for direct entry. I don't know if he played the qualies or not. If he did, he obviously lost as he didn't play in the main draw.