I have Outlook for Mac 2011 (14.5.1) that I have just loaded as I set up a new Outlook.com account.  

All email and calendar entries made on .com propagate to the my iPhone 6 Outlook App, but NO Calendar entries I create on .com sync with the Outlook Mac 2011 software and nothing I create in Outlook Mac 2011 propagates to Outlook.com.  So my Outlook 2011 Calendar is an island.. nothing in, nothing out.  All mall via the outlook.com pop server works fine.

any answers on how i can use my desktop calendar and have it connect to anything?