As far as I've been able to determine with my testing, importing City information into a record will simply take the first record in the database by that name, regardless of whether it matches Country and State/Province information also present in the record, and if none are found, will create a City record with blank Country and State/Province fields.
Before I go and duplicate the lengthy business process I wrote to handle these imports more elegantly for every object one might import address information into, I just wanted to confirm:
Is this the expected behaviour, and is there no way in the system to have imports take country and region into account when matching cities, or am I missing something?