[Jun 12, 2015 Since this article was written, Sync Services have been depreciated further. Outlook 2011 will only sync via Exchange. There is no sync for local contacts and calendars. Office 2016 Preview does not offer sync to CalDAV and CardDAV needed to sync to Apple’s iCloud or Google Contacts and Calendars.]
Based on 500+ searches today for calendar syncing, I thought I should publish the most current info on Sync Services. Currently, there is no option in Outlook’s Sync Services for Calendar events. It will be coming in a later update. Before you ask, there is no date announced.
For Outlook, we entirely rebuilt our Sync Services support from the ground up. Our goal was to take care of those issues that some heavy-duty sync users had experienced. But Sync Services is complex (just ask the engineers at Apple!). For v14.0.0, we were able to get our syncing of contacts to the level of quality that we wanted to ship with. Calendar sync didn’t meet our quality bar for release, so it’s coming in a future update.
Regards, Nadyne. Nadyne Richmond user experience researcher Microsoft Corporation Macintosh Business Unit http://www.nadynerichmond.com/blog/
If you have an Exchange account, you can set your iPhone to sync to your Exchange calendar & contacts rather than go through iCal and Address Book.
See Outlook FAQs to answer other questions you might have.
[Added Oct 21, 2010- Read The Download on Sync Services in Office for Mac 2011]