Q: Calendar syncing issues

It sounds like an issue with the connection between Outlook and the iCloud server, OR an issue with Outlook hiding your iCloud calendar.  Check your iCloud for Windows settings to make sure iCloud Mail, Contact, Calendars are being synced with Outlook.  Also, make sure the iCloud calendars are set to be displayed within Outlook itself iPhone, iPad, iPod touch: Microsoft Outlook 2003, Outlook 2007, Outlook 2010 may not display contacts and calendars afte…

Also check iCloud.com to make sure the iCloud calendar events you create on the phone are being synced to the iCloud server.  If they show up at iCloud.com then they should sync to Outlook on your PC, assuming iCloud for Windows and Outlook are both configure properly.  If everything is configured properly and the syncing still isn't working, I would suggest creating a test administrator account on your PC, setting up iCloud for Windows, and testing the iCloud calendar syncing in Outlook in this new user account.

More troubleshooting options that may be useful for you: Troubleshooting Sync Services on Windows with Microsoft Outlook 2003, Outlook 2007, or Outlook 2010 - Apple Support

Have you fixed this issue?  I'm having the same problem....