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Hmmmm, I´ve seen similar problems but not exactly the way yours is. Try the following:
Mark your calender folder and open the "View" menu, select "Current View" and then "By Category". Open the catagories displayed (click on the + symbol) and see if you can find any items with a sysmbol that looks like crossed swords. These indicate conflicting appointments, so you will need to decide which ones to keep in this case. Once you´ve removed all conflicts close Outlook. Now open the Start menu and choose run.
Type in Outlook /cleanfreebusy.
Hope this helps.
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