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Aug 11, 2014 8:23 AM in response to parkiby Jason L,Hi parki,
Welcome to Apple Support Communities.
It sounds like there is an issue syncing calendar events between your computer and iPhone. The article linked below provides a lot of great troubleshooting suggestions that should resolve the issue, including Resetting Sync History.
Troubleshooting Sync Services on Windows with Microsoft Outlook 2003, Outlook 2007, or Outlook 2010
http://support.apple.com/kb/TS2776
Reset Sync History
If you find that some of your data syncs to your device but you see an unexpected number of changes or modifications, you may reset your sync history. When you reset sync history you will be prompted to merge or replace information the next time you sync your information. To reset sync history:
- Open iTunes.
- From the Edit menu, choose Preferences.
- Click the Devices tab.
- Click the Reset Sync History button.
If the issue continues and you know all of the data is on the computer:
- Reset the Sync History again using the steps above.
- Select the device in iTunes and click the Info tab.
- Scroll down to the Advanced section, and under "Replace information on this iPhone/iPad/iPod touch" select Contacts or Calendars.
- Click Apply.
If the issue continues and you know all the data is on the iPhone, iPad, or iPod touch:
- Reset the Sync History again using the steps above.
- Remove all of the contact and calendar information from Outlook.
- Select the device in iTunes and click the Info tab.
- Scroll down to the Advanced section, and under "Replace information on this iPhone/iPad/iPod touch" make sure Contacts and Calendars are not selected.
- Click Apply.
I hope this helps.
-Jason
