There are generally no pages in HTML and thus you cannot keep your page separation when using HTML print.
The native Silverlight printing does not have that problem, but is much slower and might hang for bigger documents. If, however, you need to print a few pages and keeping the page separation is essential, you can check it out. Silverlight 5 promises to promises to introduce much faster vector-based printing, however in the meanwhile we will continue to seek a better solution for Html printing with more precise page separation.
the Telerik team
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to help you get started with RadControls for Silverlight