Generally
Via iTunes.
Connect your iPad to your comptuer, open iTunes and click on the name of your iPad. Then, in iTunes, navigate to the info tab, scroll down and you'll see the option to sync your calendars with outlook. Make the choice and sync to confirm it.
http://support.apple.com/manuals/#ipad
Might have some more info that can help
There are also some limitations based on the version of outlook that you have.
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