Hi Matthew,
Good question! The calendar does include an iCal URL that can be used to import events into an Outlook calendar. However, the plugin will not continually send updated information from that URL. If your calendar app supports RSS, The Events Calendar includes a URL for an RSS feed as well and that would send an updated feed of events.
Another thing to look into is our iCal Importer. I’m not sure if your Outlook calendar is published on the web but, if it is, and has a valid iCal URL, then you could enter that into the iCal Importer settings and have events feed from Outlook to WordPress instead.
Does this help answer your question? Please let me know. 🙂
Cheers!
Geoff