Outlook Calander sync to iPhone

You need to update your Office 2011 for Mac ot the latest update version (i.e. go into Word or any of the Office programs and go to Help/Check For Updates and process all the updates until you get to the latest 14.3.1 version. Once that's done, in Outlook under Tools, you'll see Sync Services. Enable Sync Services for the calendar to your Mac there and that will take all your stuff and put it on iCal. From there, iTunes sync can push it all to your iPhone.... or if you could upgrade your OS to do iCloud, you could then sync that portion wirelessly through that service.

That should be all there is. Calendar in OSX should then sync over to your Calendar in Outlook. Are you sure you have stuff in Calendar on OSX?

Mac iCal "On My computer" accounts are not sync-ed to external sources.

On a Mac, you need to use iCal Preferences > Accounts ...

... to specify/create where the external Server account is stored, and its type {CalDAV, exchange, MobileMe/iCloud, Google, Yahoo, other}

That's not entirely correct. I have both contacts and calendar on my iPhone which are local and not sync'd to a service other than when I sync them via iTunes to my Mac, which has Outlook configured on Sync Services to pull that info into Outlook. The only requirement for this to happen was that I had to install the updates to update Sync Services to make it work right. This is why I had suggested this to the OP. This same question was posed before by another user and this same response to them allowed it to work for them. The OP is most likely doing something wrong in the process here.

BrentROX-

"the OP" = The Original Poster.

On this thread, that's YOU!

I know nothing about how these services work on an iPhone, which is why I limited my remarks to how it works ON THE MAC.

And I never said you would have the ability to pick any calendar you have. What I said is that if your Calendar app on the Mac is in sync with your iPhone via iTunes, then those entries would be charactorized as "On My Computer". Then those would be available to be sync'd via the Sync Services option in Outlook. If that Calendar isn't charactoried as that because you're doing another type of sync with it like iCloud to get them down to your local Calendar, then they won't be available to sync over to Outlook. If that's the case, you'll have to deal with using the OSX apps for Mail/Contacts/Calendar and just using iCloud to do your syncing to your iPhone. This is a limitation that was imposed by Apple and they introduced iCloud and wanted to stop the syncing of this data over to Outlook. Like I said, the only way around this is if the info was local info not tied to an email account. There is a calendar and contacts list of such a type on your iOS device and when that gets sync'd over to your Mac via iTunes, it's the local standalone "On my Computer" choices.