Updated iTunes, had to reinstall, now Outlook Calendar is not syncing

Using an iPhone4, have not updated iOs

I installed an iTunes update recently - iTunes stopped working (was getting a missing DLL error). I have since successfully removed, then reinstalled iTunes. When I sync my Outlook Calendar, it is not syncing recent updates I added to my Outlook Calendar (on my laptop) where I always update.

Anyone have any experience with this type of issue?

Thank you.