What type of email account do you have configured in Outlook? POP, IMAP, Outlook.com, or Microsoft Exchange?
Were the calendar & contacts in a folder named “(This computer only)" ? If so, you should export to a CSV now and again for back up as they are only in that data file.
Typically, updates won't delete the ost file, but a full windows update may. Do you have a windows.old folder in file explorer? If so, see if there is a folder at C:\windows.old\AppData\Local\Microsoft\Outlook - if yes, is there a file there named with your email address?