Restoring Outlook data from Mac Time Machine

When I installed a update to my El Capitan OS, I lost my Outlook emails, calendar and contacts since May 2015. I have tried to restore from Time Machine before the catastrophe. When I restore the Main Identity, then rebuild the new version, I am left with the same 2015 data. Then I tried restoring the Main Identity from Time Machine, exporting to olm file, creating a new identity and importing the olm file. In that scenario, Outlook crashes soon after starting the import. I am really perplexed, since Microsoft support websites indicate its a piece of cake to restore the main identity from Time Machine. I have been on the phone with Apple support, but the tech didn't know anything about restoring Outlook files using Time Machine other than it should be possible. I have also spent time on the phone with a Microsoft tech. His opinion was that Outlook files could definitely NOT be restored from Time Machine because they weren't olm files. He appears to be contradicted by the Microsoft support websites, but there you go. Does anyone have step by step instructions that could help me? I would be very grateful since I am self-employed and the missing info is mostly from my business. thanks in advance!