Problem is you have two calendars on your Blackberry:
The Desktop calendar will sync with your Outlook, the Default won't. So you have to move all your calendar entries from the Default to Desktop. Do the following:
- Open the Calendar application.
- Press the menu key.
- Choose Options.
- Type MOVE on the keypad.
- When prompted to move all appointments in the base system calendar, choose YES to accept the change. All entries in the Device Default calendar will move to the default active calendar.
- Perform a hard reset of the BlackBerry smartphone by removing and replacing the battery while the BlackBerry smartphone is powered on.
After that, do the 1-way calendar sync on the BB Desktop Manager again. That should do the trick.