Outlook does not support multiple events in one iCal file. See this page
for how to include multiple events in a file usable in Outlook:
http://www.slipstick.com/calendar/holidays.htm#company

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Milly Staples [MVP - Outlook]
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| I am trying to create multiple events in an .ics (iCal) file for
| distribution to multiple users running various versions of Outlook.
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| END:VEVENT
| END:VCALENDAR