Could mean that the calendar database on the BlackBerry is corrupt. Are the entries in Outlook more up to data than the ones on the BlackBerry? If so you could try clearing the BlackBerry database, then syncing again. To clear the database on the BlackBerry, go into Backup and Restore | Advanced. On the right hand side you'll see the BlackBerry's databases. So you can select the calendar, then hit the Clear button. That will remove all the entries from the BlackBerry calendar. Afterwards try synching.
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