iTunes does not sync Outlook anymore.
OS X Server has built-in Mail, Calendar and Contacts servers. The protocols supported by Apple's server software are respectively - IMAP, CalDav and CardDav. Of these protocols all three are supported by Apple Mail, all three are supported by iOS i.e. iPhones but Outlook for Mac even Outlook 2016 only supports IMAP i.e. it does not support CalDav or CardDav.
Therefore the answer would be no.
If you had a 'real' Microsoft Exchange server then the answer would be yes, and if you have instead Kerio Connect running on a Mac then the answer would also be yes. This is because both a 'real' Microsoft Exchange server and Kerio Connect support Exchange ActiveSync aka. EAS which is what the iPhone would use, and also supports Exchange Web Services aka. EWS which is what Outlook for Mac supports. (Both 2011 and 2016 versions.)