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We have major problems with Outlook calendar at the moment and it seems that the problems you're experiencing may be something similar.
A secretary made an appointment in the calendar of a consultant. The consultant did not see this appointment when he opened his calendar. Other co-workers with acces to his calendar also did not see the appointment. Only the secretary that made the appointment sees it when she opens the consultants calendar on her laptop.
We are told that this problem with the synchronisation of Outlook calenders is caused by the fact that this secretary has a large number of mailboxes en calenders in her Outlook client and because of that a large number of folders (1000+). Microsoft apparently guarentees a proper performance of Outlook with a maximum of 500 folders.
At the moment we have several people experiencing this problem.
If this has no relevance to your case, please ignore this reply.