Sorry, but you didn't mention what printer. And from which program you are trying to print. I'll work with what I got.
First make sure that the driver you are using on the Win2k machine is the one designed for win2k for that printer.
Second, I've seen people printing from Internet Explorer having this problem when they didn't realize that thier browser was set to the largest text size. Since the pixle area or your Win2k machime might be set to much more than on the Win9x machine you don't realize that the text is actualy set to larger than on the win9x machine.