I just tried this in Word 2010 page and with Shift-Enter, that line break was ignored in the TOC, as if it hadn't been there at all. I ended up with one continuous entry in the TOC. Did you refresh the entire TOC or just the page numbers?
There might be a difference with 64-bit Office. Why are you using the 64-bit version? There are known problems with Word in that version (but none that I know about with TOC generation).
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