i think to do what you are looking for, your "left outer table" (Calendar_Table) might need to contain all possible combinations for each calendar date. I.e.:
Calendar Table would have columns: Calendar_Date, Region, Country, City
You would Left Join on all 4 columns.
What you have right now would work for a report that only shows data by Date.
You might want to google CROSS JOIN - it would produce an intentional cartesian result set that gives "all possible combinations" per date,region, country, and city.