How can I sync Outlook with my iPad?
Use iTunes to Sync Your iPad With Your Outlook Calendar.


Update iTunes in the computer to the recent version: click "Help" --> "Check for Updates."
Use the cable which comes with your iPad to connect it directly to new computer.
iTunes will launch in the PC automatically.
In the iTunes source list, select your ipad and click on "Info" tab -> the "Sync Outlook calendars" option. 
In the lower right-hand corner of your screen, you can find the "Apply" button. Click it on.
Then your computer will sync with your iPad.