Can't sync calender with outlook calender

I am trying to sync my outlook calender with my calender on my iPad but can't figure it out. When I try to go to info tab in iTunes it says this for calender option "Your calendars are being synced with your iPad over the air from iCloud. Over-the-air sync settings can be changed on your iPad." Yet my outlook calender is not syncing, nor does it sync on my iPhone either even with me selecting to sync outlook calender. I have tried to search through others and could not find one that answers my problems.

I was able to fix it somehow by deleting the calendars on my iPad and iPhone and turning off iCloud calendar it finally let me select outlook calendar to sync by also selecting to replace calendar in advanced settings. But only by selecting both. It only took 6 months for Apple to allow me to do so because I have selected the outlook calendar before and wouldn't sync.
I have Windows 7 and MS Outlook 10

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