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Refer to the following thread which discusses the same issue and check if it helps:
As mentioned before, try to rebuild the Windows Indexing options, and wait for the Indexing to complete, once that is done you may try to search in Outlook and see how the search works.
Refer to the following threads to know more:
http://windows.microsoft.com/en-US/windows7/Change-advanced-indexing-options
Though it is for Outlook 2007, it is applicable for Outlook 2010 as well.
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