Athulin hit the nail on the head.
For an investigator to not use a secondary tool to verify times and dates is quite irregular and any evidence prepared to report level would normally be checked with a fine tooth comb (Normally). For there to be such a large time discrepancy then either the tool used to perform the time and date analysis is misreporting due or unreliable. Or the data from within the file is being misinterpreted.
If it is IE then it is likely the file containing these internet search hits is in fact an Index.dat, this is a database fie used by IE to manage browsing functions including the browsing history.
This page will clarify at a basic level the time and date stamps within an index.dat file:
http://www.stevebunting.org/udpd4n6/forensics/index_dat1.htm
To answer the last part, I have never ever come across this in any examination.
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