Can no longer clear Outlook calendar

I use Outlook on my laptop (not the web version) and recently have been trying the new Outlook desktop, although I still use both.

I like to send my calendar from work (on a work laptop) to myself at home as an exported *.csv so that I can see my work calendar events on my personal calendar, and I use the outlook.com service for my personal calendar and email.

I used to be able to clear my old calendar on old outlook by switching to list view, selecting everything with ctrl A and then deleting.  I could then import the *.csv file and create my entire calendar at home.

This isn't working at all well anymore.  I can still do this with classic Outlook, but somehow this has set a "different" calendar in the new Outlook.  In other words, I see a calendar in the New Outlook that I don't see in Outlook classic (for the exact same account at outlook.com).  It's just all fouled up.

Does Microsoft have any sort of support for their outlook.com service whatsoever because it just seems like they don't remotely care or support it.

Gene