I don't use Outlook, so I don't know, but you could try reversing the 
folder sort order and do another drag and drop and see if affects the order 
in which they are transferred.

It seems that in Thunderbird, the folder sort order has no effect.  In all 
cases, the transfer order from old folder to new folder is based on arrival 
order in the old folder -- least recent is transferred first (which is what 
you want).  So if you still have the messages on the old server, you could 
try using Thunderbird to move them over.

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