Outlook presumes (rightly or wrongly) that you remember the most recent
events and need to find those older ones that you have forgotten about.
Therefore, search is from oldest to newest.

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Milly Staples [MVP - Outlook]
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After furious head scratching, Mukman asked:
| When searching Activities in Outlook, it should start search from most
| current activity.
[quoted text clipped - 7 lines]
| button, follow this link to open the suggestion in the Microsoft
| Web-based Newsreader and then click "I Agree" in the message pane.
http://www.microsoft.com/office/community/en-us/default.mspx?mid=afed3cb8-3140-4
175-b1de-2c2e3e733492&dg=microsoft.public.outlook.contacts